Coordination Chemistry Reviews 426 (2021) 213542
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Coordination Chemistry Reviews
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Review Metal–organic frameworks based on multicarboxylate linkers
Hosein Ghasempour a, Kun-Yu Wang b, Joshua A. Powell b, Farnoosh ZareKarizi a, ⇑ ⇑ Xiu-Liang Lv b, Ali Morsali a, , Hong-Cai Zhou b,c, a Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14155-4838, Tehran, Iran b Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, United States c Department of Materials Science and Engineering, Texas A&M University, College Station, Texas 77843-3003, United States article info abstract
Article history: When designing metal–organic frameworks (MOFs), linker design is one of the most important factors in Received 8 July 2020 constructing a wide variety of structures. Judicious choice of linker size, geometry, and connectivity can Accepted 5 August 2020 create diverse structures and topologies, which can aid in the quest to design MOFs with both high sta- Available online 29 August 2020 bility and permanent porosity. Multi-connected linkers have become a focus in the MOF community, as high connectivity can improve stability and tunability of frameworks. In particular, multicarboxylate ligands have been reported extensively in the literature to construct stable MOFs with versatile pore environments, which can be termed as metal-multicarboxylate frameworks (MMCFs). These structures have great application potential in gas adsorption and separation, catalysis, and sensing. Herein, we
review the literature on multicarboxylate linkers (nCOOH 3) in MOF systems and their applications, with specific emphasis on how high linker connectivity affects properties of MOFs such as topology, porosity, stability, and functionality. Ó 2020 Elsevier B.V. All rights reserved.
Contents
1. Introduction ...... 2 2. Topological and structural properties of MMCFs ...... 2 3. Porosity in MMCFs ...... 8 4. Stability in MMCFs ...... 15 5. Flexibility in MMCFs ...... 16 6. Mixed linker MMCFs ...... 17 7. Synthetic methods in MMCFs ...... 18 8. Functionality in MMCFs ...... 19 9. Applications of MMCFs ...... 21 9.1. Gas storage and separations ...... 21 9.2. Catalysis ...... 22 9.3. Sensing...... 23 9.4. Water adsorption ...... 23 9.5. Biological applications ...... 23 9.6. Other features of MMCFs ...... 24 10. Conclusion and perspective...... 25 Declaration of Competing Interest ...... 25 Acknowledgment ...... 25 Appendix A. Supplementary data ...... 25 References ...... 25
⇑ Corresponding authors at: Department of Chemistry, Faculty of Sciences, Tarbiat Modares University, P.O. Box 14155-4838, Tehran, Iran (A. Morsali); Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, United States (H.-C. Zhou). E-mail addresses: [email protected] (A. Morsali), [email protected] (H.-C. Zhou). https://doi.org/10.1016/j.ccr.2020.213542 0010-8545/Ó 2020 Elsevier B.V. All rights reserved. 2 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
1. Introduction are other advantages of MOFs containing multicarboxylate linkers. Unfortunately, the complex and unpredictable structures of While coordination polymers composed of metal nodes and MMCFs can impede further study. organic linkers were firstly studied in the mid-20th century, the In addition to providing a general summary of reported MMCFs first permanently porous coordination polymer, commonly known (Schemes 1–6, Tables 1–6), this context aims to investigate the as a MOF, was not reported until the 1990s [1–8]. Upon the discov- structural consequences of multicarboxylate linkers in MOFs, such ery of MOFs, these materials became the center of attention for as their influence on topology, porosity, stability, flexibility and the researchers across diverse fields [9–11]. Their high porosity, effectiveness of the MOFs in a range of applications. extreme versatility and structural tunability provide multiple advantages over other porous materials like activated carbons or zeolites for diverse applications such as catalysis [12–18], gas stor- 2. Topological and structural properties of MMCFs age and separation [19–21], energy applications [22,23] and sequestration of toxic chemicals [24,25]. One of the earliest MOF Knowledge, prediction, and classification of network topology was published in 1999, with the framework comprised of zinc are important for designing novel MOFs with specific characteris- acetate (Zn4O(COO)6) clusters and the well-known ditopic linker tics and, as such, topological exploration in MOFs has become an benzene dicarboxylate (BDC2 ) [26]. Further studies elaborated important focus of MOF chemists in recent years [53–55]. Design- on this design to form a series of isoreticular MOFs (IRMOFs) by ing the network topology in MOFs can be done within two main substituting BDC2 with other ditopic linkers in a process known routes, changing the cluster connectivity or altering the linker’s as reticular synthesis [27]. Despite the potential of these materials, topological geometry. Metal clusters adopt established geometries the susceptibility of the zinc acetate cluster to hydrolysis limits which cannot be easily modified to change connectivity. Therefore, their applicability in gas adsorption and separation, as these logical designing of linker geometry is essential for discovering processes often take place in humid environments [28,29]. This specified topologies as an ideal platform for designing MOFs. drawback inspired design of MOFs containing binuclear Choosing linkers with flexible branches, desired dihedral angles,
M2-paddlewheel clusters (M = Zn or Cu), which show improved and topological shapes are among the advantages of using multi- water stability. Although the assembly of these clusters with carboxylate linkers. One exciting study was the discovery of the
H2BDC-type ditopic linkers always leads to a 2D layered coordina- gea net as an ideal blueprint net by Guillerm et al. Their geometri- tion polymer instead of a 3D framework, the combination of a cal analysis of the gea-a net revealed that transposition of pre- tricarboxylate linker, benzene tricarboxylate (BTC3 ), and a copper known copper paddlewheels eto MOP [56] into the anticipated paddlewheel cluster led to the highly porous and stable 3D frame- gea-MOF platform required the employment of a multicarboxylate ° work HKUST-1 ([Cu3(BTC)2 3H2O]n), which served as a benchmark ligand with two branches that contain 120 angle dicarboxylic acid in adsorption studies for many years [30,31]. extremities and a third branch with a 90° angle dicarboxylic acid The high stability and porosity of HKUST-1 has spurred research extremity. Consequently, 50,50000-((5-((4-(3,6-dicarboxy-9H-carba into the design of other MOFs with multicarboxylate linkers, zol-9-yl)phenyl)ethynyl)-1,3-phenylene)bis(ethyne-2,1-diyl))bis known as metal multicarboxylate frameworks (MMCFs). Today, ((1,10:30,100-terphenyl]-4,400-dicarboxylic acid), a hexacarboxylate multicarboxylate ligands are widely used in MOF synthesis, and a ligand with 120° and 90° angles (in a ratio of 2:1), was rationally large number of MOFs have been successfully constructed using designed for both the fabrication of the targeted eto MOP and 3D tritopic [30,32,33], tetratopic [34–37], pentatopic [38–41], hex- 18-connected gea-MOF-2 [57]. In another work, the Hupp group atopic [42–45], octatopic [46–48], and even dodecatopic carboxy- showed that the well-established 6-c acs topology (the assembly late ligands [49–51]. The geometries of multicarboxylate linkers of trigonal prismatic metal clusters and ditopic ligands i.e., are dictated by several factors, including the degree of deprotona- MIL-88, MIL-235) can also be synthesized using suitable trigonal tion, hydrogen bond donor/acceptor behavior, size, rigidity, prismatic hexatopic organic ligands in the presence of trigonal whether the carboxylates are coplanar, and the presence of other prismatic trinuclear metal nodes. They introduced a series of functionalities on the ligand [52]. Generally speaking, the most noncatenated acs-MOFs (NU-1500) with uniform hexagonal important advantages of incorporating multicarboxylate linkers channels [58]. into MOFs are enhanced stability and rigidity through higher con- Several reports on the design of isoreticular (IR) structures with nectivity with metal nodes (Fig. 1). Higher porosity, decreased ditopic linkers and diverse clusters has been published, leading to dead space in pores, reduced interpenetration, and improved tun- series of MOFs with the same underlying topologies as one another ability of the pore environment through linker functionalization but linkers with different sizes or pendant functional groups. The development of IR series with ditopic linkers allows the rational construction of networks with high porosity and specific topolo- gies [27,59,60]. Although such linker extension can be an effective approach to increasing pore volume, networks with long linkers, and hence large pores, are prone to interpenetration, which decreases the empty space in the pore, as observed in IRMOF-11, IRMOF-13 and IRMOF-15 [27]. This drawback can be overcome by using multicarboxylate linkers. Due to the complexity of these ligands, the high connectivity and specific geometry can prevent interpenetration through the construction of topologies that are intrinsically unfavorable towards interpenetration [61,62]. For
example, the simple Zn4O clusters usually form pcu network with ditopic linkers, while the combination of tritopic linkers with this cluster forms qom networks such as MOF-177 [63]. Enlarging the linker as in MOF-180 lead to non-interpenetrated structures with the same topology [32]. Fig. 1. Multicarboxylate linkers lead to more robust metal–organic frameworks as a On the other hand, the branched multicarboxylate linkers can result of higher connectivity. adopt more conformations and topological geometries in H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 3
Scheme 1. Tricarboxylate linkers. 4 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Scheme 2. Tetracarboxylate linkers. H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 5
Scheme 2 (continued) 6 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Scheme 2 (continued)
topology [66]. This linker with planar geometry (no dihedral rota- tion) led to MOF-525 with ftw topology [67]. When linker geometry and cluster connectivity are more complicated, it becomes more challenging to design MMCFs with a predetermined topology [68]. Highly connected networks, such as 8-, 12-, or even 20-connected nets are highly desirable due to their enhanced stability. A statistical analysis on reported topolo- Scheme 3. Pentacarboxylate linkers. gies indicates that the majority of MOFs containing coplanar tri-, tetra-, hexa- and octa-topic linkers exhibit one of only a small number of topologies. This indicates that high-connected, high comparison with ditopic linkers, which causes more points of symmetry structures can be formed in a predictable fashion with extension in these linkers, resulting in high connected and ultra- relative ease when using multitopic linkers. Fig. 3 shows the porous structures. For instance, the hexadentate linker MeTDCPB6 prevalence of the most commonly reported topologies in planar (2,4,6-trimethyl-1,3,5-tri(3,5-di(4-carboxyphenyl-1-yl)phenyl-1-yl)- multicarboxylate MOFs according to the Reticular Chemistry benzene) can take both octahedral and trigonal prismatic geometry Structure Resource (RCSR) [69]. in the presence of Zn4OandPb6 clusters, forming JUC-103 and As shown in Fig. 3, the number of donating groups and the JUC-104 with an unusual (6–12)-connected CaSi2 topology [64]. geometry of the linkers have a large influence on the final network For a given metal node, the topological and structural features topology. Among multicarboxylate linkers, hexacarboxylate linkers of the framework is largely dictated by the geometry and connec- exhibit the least topological variety, which can be attributed to the tivity of the selected organic linkers. Small variations in ligand size similarity in linker shapes. Most reported hexacarboxylate linkers and shape, especially the dihedral angle between the central and form MOFs with rht networks, which are ideal prototypes for the peripheral rings, may lead to hundreds of diverse net topologies. development of novel MOF structures with large pores, high stabil- This can be an obstacle for the construction of new IRMOFs, as even ity, ultrahigh surface area, and no framework interpenetration. It is small changes to the linker can generate different topologies. As often useful to describe rht-type MOFs in terms of the molecular reported by Zhou and coworkers, simple changes in the identity and supermolecular building blocks that are used to construct and location of substituents on a tetratopic linker can result in them. The fundamental molecular building blocks (MBBs) of MOF structures with three different net topologies: flu, scu, and rht-type MOFs are M2(carboxylate)4 paddlewheel clusters and csq [65]. The rotation of the central and peripheral rings in these triangular hexacarboxylate ligands. These MBBs can be combined linkers is shown in Fig. 2. A similar report by the Yaghi group on to construct highly symmetric 24-connected polyhedra, termed PCN-222 showed that dihedral rotation of benzene rings in the as supermolecular building blocks (SBBs). When SBBs are further tetracarboxylate TCPP ligand (rotated 35.888° from the angle combined to create an extended structure, they form the enclosed observed in the free ligands) provide a compatible geometry to polyhedral cavities and 3D interconnecting channels of the MOF. connect the Zr6 clusters to generate a 3D network in Kagome-like This type of framework contains a high density of open metal sites H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 7
Scheme 4. Hexacarboxylate linkers. 8 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 pointing toward the center of the polyhedron. The rht network is corresponding MOFs. Furthermore, pore modulation and reticular unique because of the absence of interpenetration and its procliv- chemistry approaches are difficult due to the steric congestion ity towards isoreticular expansion, where higher surface areas and and geometric diversity possible in such a complex linker. larger free pore volumes can be easily achieved through expansion Despite these challenges, octatopic ligands can be used to pro- of the bifunctional organic linker [70,71]. The rht-MOF platform duce new MOFs with improved porosity and stability. As there can be tuned through several simple pathways: (1) C3-symmetric are few octacarboxylate MOFs in the literature, the structural expansion of the triangular MBB to increase the spacing between properties and topologies of these highly connected struts
SBBs, (2) C3-symmetric or asymmetric expansion of the triangular remain relatively unstudied. Most of the octacarboxylate MOFs MBB to expand the SBB, (3) modification of the core of the triangu- in the literature feature one of two topologies, scu or tbo.An lar MBB, and (4) functionalization of the MBBs [72–74].C3- scu topology is generated if the 4-connected paddlewheel SBUs symmetric hexacarboxylate linkers commonly form rht networks, and linkers are viewed as 4- and 8- connected nodes respec- as reported in the NOTT-13, NOTT-14 and NOTT-15 series [71], tively. In this case, the framework can be simplified as a (4,8) NOTT-119 [75], NU-125 [76], NU-111 [77], and PCN-69 [78].In net with scu topology. These structures compose approximately addition to their tunability, high density of open metal sites, and two fifths of reported octacarboxylate MOFs (Fig. 3). There are a lack of interpenetration, rht networks contain multiple cavities similar number of structures containing octatopic linkers that of different sizes within the framework. These key features can form a tbo topology, which is an analogue of the (3,4-c) tbo be exploited for storage applications across a wide range of pres- topology exhibited by HKUST-1 [92–95]. This topology was first sures. Other unique topologies can also be observed in MOFs with reported for octacarboxylate MOFs by Eddaoudi and coworkers hexacarboxylate linkers such as UTSA-20, which has zyg topology using quadrangular organic ligands [96]. The potential for poros- and shows high methane adsorption [42]. ity modulation and functionalization of non-interpenetrated Tetracarboxylate linkers show a greater diversity in topology structures make these structures promising candidates for appli- than hexacarboxylate linkers due to more diverse linker symmetry. cations such as methane adsorption.
Some linkers have a tetrahedral shape with an ideal Td symmetry, MOFs with tricarboxylate linkers have the greatest topological which is the highest symmetry that can be attained by any tetrato- diversity among multicarboxylate MOFs due to various symme- pic linker. In some cases, tetrahedral linkers are desymmetrized to tries (planar or twisted) and coordination modes. The tbo network lower symmetries while maintaining an approximately tetrahedral is the most studied topology among these structures. One of the shape or distorted to form C1 symmetric distorted tetrahedra via a most well-known tbo networks, HKUST-1, features high perfor- molecular pivot hinge approach [79,80]. Alternatively, linkers can mance across a range of applications [30]. This exceptional perfor- take a square planar shape, which has an ideal D4h symmetry mance has motivated the production of similar networks, as and is frequently found in the important class of porphyrin- demonstrated by Yaghi and coworkers, who showed that HKUST- based linkers. As with tetrahedral linkers, square planar linkers 1 like topologies can be obtained through linker extension [97]. can be desymmetrized, in this case to a rectangular D2h symmetry. For example, the highly porous tbo network MOF-399 exhibits 3 Some flexible planar linkers can form both square (D4h) and rectan- large void space (94%) and low crystal density (0.126 g/cm as cal- gular (D2h) shapes through deformation. Likewise, linkers can culated) (Fig. 5). Such reports indicate that the tbo topology can be access both planar shape and tetrahedral shapes through rotatable achieved by isoreticular chemistry using tritopic linkers to form CAC linkage between two aryl rings (Fig. 4) [68]. highly useful building blocks. Among various MOFs with tetracarboxylate linkers, nbo-type In addition to these common networks in MMCFs, reports on MOFs have been extensively explored. The M2+ ions form paddle- rarer topologies indicate that the use of multicarboxylate ligands wheel M2(COO)4 clusters, which serve as square-planar secondary can lead to frameworks with novel topologies and enrich the building units (SBUs) linked with the rectangular linkers. This gives library of MOF topologies [98]. For instance, Eddaoudi and cowork- rise to a 3D nbo-type network. This topological arrangement of ers combined rare earth (RE) metal salts with tricarboxylate building units leads to non-interpenetrated structures with high ligands to obtain highly connected networks with pek and aea surface area, open metal sites, tunable pore sizes and readily acces- topologies for hydrocarbon separations [99]. In another study, sible void spaces [81]. Enhanced interactions of nbo-type frame- the application of non-linear silicon-containing tetracarboxylate works with gas molecules make them suitable for gas adsorption linkers with copper ions forms a framework with a previously studies, especially methane storage, with examples such as MOF- unreported chs topology. The narrow pores of this network present 505 [82], MOF-101 [83], UTSA-80 [84], PCN-16 [85], NOTT-105 promising opportunities for small molecule separation [100].In [86], and NU-135 [87]. The Zhou group has also reported several 2013, Qian, Chen and coworkers utilized a slightly bent tetratopic 0 nbo-type MOFs incorporating anthracene derivatives and double linker (5,5 -(9H-fluorene-2,7-diyl)diisophthalic acid (H4FDDI) and bond or triple bond moieties that show good methane adsorption paddle-wheel [Cu2(COO)4] clusters to synthesize a MOF dubbed properties [85,88,89]. ZJU-25 [101]. ZJU-25 displays a very rare sty-a framework topology The tunable void spaces and diverse cavities formed in nbo- and exhibits moderately high porosity, with a Brunauer-Emmett- MOFs also make them good candidates for efficient gas separation, Teller (BET) surface area of 2124 m2 g 1. Additionally, a series of as these structures typically have high gas adsorption performance. mesoporous MOFs with a rare corundum topology and tunable The He group carefully optimized the pore structure of an nbo- cage sizes were rationally constructed by Xu group [102]. In this 0 type MOF, ZJNU-53a ([Cu2L(H2O)2]∙6DMF 2H2O, L = 5,5 -(naphtha work, four types of flexible tetratopic ligands were combined with lene-1,4-diyl-ethyne-1,2-diyl) diisophthalic acid), by modification Td-symmetric [Zn4(COO)6O] clusters, respectively. This series of of the tetracarboxylate linkers. The group found that the optimized MOFs possesses high CO2 uptake capability which increases with MOF exhibited exceptionally high volumetric methane storage and larger cage sizes. working capacity [90]. Although highly connected rigid linkers have been widely explored in development of reticular chemistry for tetra- and 3. Porosity in MMCFs hexacarboxylate linkers, few reports exist on octacarboxylate MOFs. The first example of porosity modulation in IRMOFs with MOFs can be distinguished from other coordination polymers octatopic linkers was reported in 2017 [91]. Synthesis of octato- by their high porosity. Numerous attempts have been made to pic linkers is typically complex, hindering attempts to design the understand the nature of these pores and increase their volume H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 9
Scheme 5. Octacarboxylate linkers.
Scheme 6. Dodecarboxylate linkers. 10 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Table 1 Table 1 (continued) Tricarboxylate linkers and their corresponding MMCFs. H3L Corresponding MMCFs References H3L Corresponding MMCFs References H3L75 [[Cd3(L)2(H2O)(THF)] 2THF]n [382–385]
H3L1 [Mn3(C6H5O6)2(H2O)4]n [271] H3L76 [Tb(BCB)(DMF)] (DMF) [386,387]
H3L2 [KCo3(C6H4O7)(C6H5O7)(H2O)2] [272] H3L77 [Ln(L)(H2O)(NMP)] 1 .5H2O [388]
H3L3 [Ln(NTA)(H2O)] [273] H3L78 [Ln(TTTPC)(NO2)2(Cl)], SCU-7 [389,390] H3L4 [Er(CTC)(H2O)2] 2 .5H2O [274–276] H3L79 [(NiL)3(BTCMT)2] DMF 16H2O [377,391,392]
H3L5 (HKUST-1), MIL-96, MIL-100 [30,277–282] H3L80 UMCM-151 [39,393]
H3L6 [Mn2(OH)(H2O)(PTC)] [283,284] H3L81 YZU-103 [394]
H3L7 [Cu3(NH2-btc)2] [285–287] H3L82 UPC-30 [395,396] H3L8 [[Cd3(OABDC)2(H2O)5] 2H2O]n [262] H3L83 [Co(L)]n [397]
H3L9 [Zn4(OH)2(1,2,4-BTC)2] [288,289] H3L84 PCN-909 [80] H3L10 [Er(PZTA)(H2O)4] 2H2O [290] H3L85 Cu3L2 3H2O [398]
H3L11 [Zn2(OABDC)(OH)]n [291] H3L86 UPC-33 [399] H3L12 Zn2(BOABA)(OH) H2O [292] H3L87 [Y2(bpa)2(H2O)3] [400,401]
H3L13 [Cu3(TMBTA)2(DMA)(H2O)2] [293] H3L88 [Mn3(L)2(H2O)4] [400]
H3L14 [Zn3(tci)2(DMF)2)] [294,295] H3L89 [Cd4(OH)2(L)2(H2O)3]n [400,402] H3L15 Ln(bta) nH2O [296] H3L90 PCN-99 [403]
H3L16 [Ln2(TCT)2(H2O)6].6H2O [297] H3L91 POST-65 [404,405]
H3L17 [Cd8Na(ntc)6(H2O)8] [298] H3L92 Cd1.5(H3O)3[(Cd4O)3(hett)8] 6H2O [406] H3L18 [Zn(HTPO)] 6H2O]n [299] H3L93 [Zn4O(hmpib)2] (UCY-1) [407]
H3L19 [Cd1.5(L)]n [300] H3L94 UTSA-28 [408]
H3L20 ZJU-35 [301] H3L95 BUT-13 [143]
H3L21 ZJU-36 [301] H3L96 MOF-180 [32,166]
H3L22 ZJU-199 [302] H3L97 [Mn3(LMe)2(DMF)4(H2O)] [409]
H3L23 BUT-70, Ln-BTPCA [303,304] H3L98 SUMOF-7IV [32]
H3L24 [Cu4(HL)2(H2O)4(MeO)4]n [305,306] H3L99 [Zn6(C33H18N9O6)4(H2O)3]n [221]
H3L25 [[Cd[(S)-PIA](HDABCO)]n [307–310] H3L100 MOF-200, MOF-399 [97,166] H3L26 [Co(H2O)6][Co2(dcpct)2(H2O)6] 2H2O [311] H3L101 [Zn2(OH)L] 2DMF 2H2O [410,411] H3L27 [LnL(H2O)3] 3H2O 0.75DMF [312] H3L102 MOF-388 [97] H3L28 [Tb(L)(DMA)] (DMA) (0 .5H2O) [313] H3L103 [LnTCM(H2O)2] 3DMF H2O [158,412]
H3L29 ZJU-197 [314] H3L104 [Zn2(L)(H2O)] (NO3) 0.2DMF [413]
H3L30 [Zn3(L)2(H2O)2]n [315] H3L105 [Zn2(L1)(H2O)] (NO3) DMF [413]
H3L31 UMCM-150 [316,317] H3L106 [Cd2(L)(H2O)3](NO3)0.7(HCOO)0.2Br0.1 [414]
H3L32 (M3(L)3(H2O)4], M = Tb, Dy, Er [318,319] H3L107 Cd(HL)(H2O)2 [414] l H3L33 [Cd3(L)2( 2-H2O)2] (H2O)3 [320] H3L108 SNU-150, SNU-151 [415]
H3L34 [Cd3(ABTA)2(DMF) (H2O)2] [321] H3L109 ZJNU-30 [416] H3L35 [LnL(H2O)2] DMF H2O [322] H3L110 ZJNU-31, UTSA-30 [416,417] H3L36 [Zn4O(L)2 (H2O)3] 3DMA 3EtOH 6H2O [265,323] H3L111 MIL-103, MIL-112 [418] H3L37 [La(TPT)(DMSO)2] H2O [324,325] H3L112 [Zn2(L)(DMA)2(CH3COO)] [419] H3L38 [[La(cpia)(2H2O)] 4H2O]n [326,327]
H3L39 [(La)(H2O)(DMF)3(L)] H2O [328]
H3L40 [Mn3(L)2(H2O)(DMF)2] [329]
H3L41 [LnL (HCOO)H2O] [330]
H3L42 [Tb(PTMTC)(EtOH)2H2O] xH2O [331] Table 2
H3L43 (MOF-150), MOF-515, MOF-516 [32,332–335] Tetracarboxylate linkers and their corresponding MMCFs.
H3L44 UPC-15, [Cd3(L1)2(DMA)2] DMA [336–339] H4L Corresponding MMCFs References H3L45 [Zn1.5(L)(H2O)3(NH2Me2)NO3](DMF)0.5 [340]
H3L46 UO2(HL) (UOF-1) [341] H4L1 Cd2(CBTC)(H2O)2]n [420]
H3L47 [Zn2[MeSi(PhCO2)3](OH)(DEF)2] [342] H4L2 [Li6(HTFTA)2(H2O)3] 3H2O [421,422]
H3L48 [Ln(TPO)] [343] H4L3 [Mn2(l4-L)(H2O)6] [423,424]
H3L49 PCM-48 [344] H4L4 MIL-118 [425,426] l l H3L50 Zr6( 3-O)4( 3-OH)4(H2O2)(L)4 [345] H4L5 [Ln4(pztc)3(H2O)11] [427–429]
H3L51 [Zn4(OH)2(PTBC)2(DMF)(EtOH)]n [346] H4L6 [cis-K2Zn2Mn(l7-pdtc)2(H2O)10 [430]
H3L52 Zn2(mptbc)2(dmf)(OH2)] [346] H4L7 [[La2(L)1.5(H2O)4]∙2.75H2O]1 [431]
H3L53 PCN-53, MIL-150 [347–349] H4L8 UTSA-60 [211]
H3L54 PCN-20 [350–352] H4L9 MOF-34 [432–434]
H3L55 Y-aea-MOF, DUT-75, DUT-76 [99,353] H4L10 [Zn5(DpImDC)2(DMF)4(H2O)3] [435] H3L56 Zn3(BTPCA)2(H2O)3 py 3DMSO [354] H4L11 [[Cd5(bta)4] 6H2NMe2]n [436]
H3L57 JUC-125 [355] H4L12 [(CH3)2NH2][In(L)] [437]
H3L58 MOF-143, MOF-177, MOF-519, MOF-520 [57,356–359] H4L13 MOF-505/NOTT-100, MFM-300 [61,183,438–441]
H3L59 NU-1301, NU-1200, BUT-12 [143,188,217] H4L14 [Ln(Hdpda)(H2O)4] [442,443]
H3L60 PCN-6, PCN-9, PCN-117, PCN-333 [33,360–363] H4L15 [Mn4(BPTCA)2(H2O)10 2.5H2O]n [444,445]
H3L61 [Cu3(m-TATB)2Py(CH3OH)2] [364] H4L16 PCN-11, BUT-28 [446,447]
H3L62 PCN-604, SUMOF-5 [209,32,365] H4L17 PCN-10, JUC-62, UPC-22 [182,446,448,449]
H3L63 MOF-177-X, MTV-MOF-177 [63] H4L18 [M2DBIP-(H2O)4(l2-H2O)] [450]
H3L64 R- PCN-333(Fe) [366] H4L19 NJU-Bai 17 [451]
H3L65 PCN-308 [367] H4L20 [Cu6(L)3(DMF) (H2O)5]n (DMF)x [452]
H3L66 NU-700 [368] H4L21 Cu2(EBTC)(H2O)2 [453] H3L67 [Zn3(HTB)2(H2O)2] 3DMA 5H2O [369,370] H4L22 PCN-46 [89]
H3L68 DUT-77 [371] H4L23 NOTT-101 [61]
H3L69 truMOF-1, truMOF-2 [372] H4L24 UTSA-88 [212]
H3L70 BUT-39 [373,374] H4L25 ZJU-5 [207,454]
H3L71 PCN-101 [375,376] H4L26 Yb-DDIA [454]
H3L72 meso-MOF-1, PCN-100 [106,377,378] H4L27 [Co3(L)(l3-OH)2(H2O)4] [455]
H3L73 CTGU-2, GTUC-7 [268,379] H4L28 [Cd(H2La)0.5(H2Lb)0.5(H2O)] [456]
H3L74 [Cd3(L)2(H2O)6] [380,381] H4L29 Ln(HL)(H2O)(DEF) [451,457] H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 11
Table 2 (continued) Table 2 (continued)
H4L Corresponding MMCFs References H4L Corresponding MMCFs References
H4L30 NOTT-105 [86] H4L105 ZJNU-87–89 [506]
H4L31 NOTT-106, ZJU-11 [86,458 459] H4L106 Zn-ATTA [507]
H4L32 Cu2(TPTC-OR) [201] H4L107 ZJU-195-NH2 [508]
H4L33 NOTT-107, UPC-8 [86,460] H4L108 PCN-305 [509]
H4L34 NOTT-108 [86,461] H4L109 PCN-307 [509]
H4L35 [Cu(C13H7O5)(H2O)]n (QI-Cu) [462] H4L110 PCN-308 [509]
H4L36 ZJU-10 [463] H4L111 ZJU-195, PCN-306 [510]
H4L37 UTSA-90 [464] H4L112 ZJNU-54 [193]
H4L38 UTSA-75 [465] H4L113 ZJNU-55 [195]
H4L39 UTSA-76, NZJU-47 [207,466] H4L114 [Zn2(L)(H2O)1.5] 5H2O [511] 0 H4L40 ZJU-40 [206] H4L115 PCN-12, PCN-12 [512]
H4L41 ZJU-56 [467] H4L116 PCN-12-CO [204]
H4L42 ZJU-8 [468] H4L117 FJI-C4 [513]
H4L43 NJU-Bai 19 [469,470] H4L118 PCN-12-Si [514]
H4L44 [Cu2(L)(H2O)2] [13] H4L119 [Cu3(L)2(DMF)] [515]
H4L45 NOTT-109, ZJU-7 [86,471] H4L120 [[Ln2K2(dcppa)2(H2O)6] mH2O]n [233]
H4L46 ZJNU-43 [472] H4L121 [ZnCa(dcppa)(DMF)2]n [516]
H4L47 ZJNU-44 [472] H4L122 MIL-102, Er2(Ntc)1.5(H2O)5] 6H2O [517,518]
H4L48 ZJNU-45 [472] H4L123 [Ln3(l3-O)(H2O)3(PTC)1.5]n [519]
H4L49 ZJNU-40 [219] H4L124 [Mg16(PTCA)8(l2-H2O)8(dioxane)8]n [145]
H4L50 ZJU-9, NJU-Bai 41 [473] H4L125 Zn-HFDT [520]
H4L51 [[Eu2L1.5(H2O)2EtOH] DMF]n [214] H4L126 Ln-TETA [521,522]
H4L52 [[Cd1.5(C18H10O10)] (H3O)(H2O)3]n [474] H4L127 MMCF-1, MMCF-2, MMCF-3 [523–525]
H4L53 ZJNU-50 [475] H4L128 MIL-133 [526]
H4L54 UHM-8, NJU-Bai12 [115,123] H4L129 Zn2(TTFTB) [527,528]
H4L55 NOTT-102 [61] H4L130 [Ca2L(CH3OH)2(H2O)2] [529]
H4L56 MFM-130 [196] H4L131 [Zn4-(dcpp)2(DMF)3(H2O)2]n] [530]
H4L57 [Cu2L(H2O)2] (NO3)2 5.5H2O [476] H4L132 [Cu2(BCP)(H2O)2] 3DMF]n [531]
H4L58 [Cu2(bdfdpa)(H2O)2] (JLU-Liu29) [477] H4L8133 [[Fe3(ACTBA)2]X 6DEF]n [146]
H4L60 ZJNU-53 [90] H4L134 HNU-22, (Et2NH2)-[In(BCBAIP)] 4DEF 4EtOH [532–534]
H4L61 MFM-102-NH2 [478] H4L135 ZJU-32 [116]
H4L62 MFM-102-NO2 [478] H4L136 NU-GRH-1 [535]
H4L63 Cu2(OFDI) (ZJU-61) [120] H4L137 DUT-12 [536]
H4L64 NOTT-110 [210] H4L138 NPF-300 [537]
H4L65 NOTT-111 [210,479] H4L139 ZJU-31 [197]
H4L66 [Cu2(FDDI)] (ZJU-25) [101] H4L140 FJU-16, FJU-17, Cu2(pbpta) [538,539]
H4L67 NOTT-104 [86] H4L141 PCN-81, 82 [540]
H4L68 MFM-131 [196] H4L142 PCN-14 [88]
H4L69 [[Co2(pdpa)(CH3CN)(H2O)3] [480] H4L143 [Zn2(L)(H2O)2] [180,541]
H4L70 NOTT-103 [86] H4L144 [[Ni(H2BTTB) (H2O)2] (DIOX)2]n [542,543]
H4L71 [Cu2(NDED)(H2O)2] xS [81] H4L145 Zn-TCPP [234]
H4L72 NJU-Bai43 [473] H4L146 Y-csq-MOF-1 [544]
H4L73 PCN-426 [481] H4L147 Cu2(D2-TCPPDA)(H2O) [545–547]
H4L74 UTS-110 [482] H4L148 DUT-80 [548]
H4L75 NU-135 [87] H4L149 ZJU-30, PCN-605, MFM-202, NOTT-202 [35,197,549,550]
H4L76 NU-150, 151, 152 [98] H4L150 PCN-606, UTSA-67, FJI-H11 [549,551,552] 3 8 H4L77 [[M(bdcbpy)(OH2)4] 4H2O]n [483] H4L151 Lc-Zr6-bcu [553]
H4L78 [ML] 2H2O [484] H4L152 [Zn1.5(L)(DMF)] [165]
H4L79 [Cu2[(C20H12N2O2)(COO)4]]n [485] H4L153 [Cu2L(H2O)2] 13DMF [554]
H4L80 [Cd2(H2L)2(H2O)5], NKU-105 [232] H4L154 [Cu2(L)(H2O)2] 13DMF [555]
H4L81 ZJU-15 [486] H4L155 [Cu2(L)(H2O)2] 12DMF [555]
H4L82 PCN-124 [487] H4L156 [Cu2(m-TCPB)(H2O)2]n [(DEF)3]n [556,557]
H4L83 [Cu2L(H2O)2] Sn [488] H4L157 UMCM-152, 153 [39]
H4L84 [Ln(HL)(DMA)2] DMA [489] H4L158 BUT-62 [558]
H4L85 [InL][(CH3)2NH2] [490] H4L159 BUT-63 [558]
H4L86 JLU-Liu 20, JLU-Liu 21 [192,491] H4L160 DUT-71, DUT-117 [558,559]
H4L87 [Cu2(IMTA)(DMSO)2] [492] H4L161 PCN-21 [560]
H4L88 [Cu6(DDC)3(S)6] [493] H4L162 PCN-38–39 [561]
H4L89 [[Ba2(BDPO)(H2O)] DMA]n [191] H4L163 Cu2(H2O)2(ADBTD) xS [270]
H4L90 ZJU-26 [144] H4L164 [Co2(L2)(MeOH)(H2O)4]n [562]
H4L91 Zn28L112(H2O)28] [494,495] H4L165 NU-1000, NU-1300 [36,269,563]
H4L92 UHM-6 [496] H4L166 Zr6O4(OH)4(TCBPPy)3 [238]
H4L93 [Cu24(L)12(H2O)16(DMSO)8]n [100] H4L167 NU-1100 [213]
H4L94 ZJNU-51 [497] H4L168 NU-1006, NU-1103 [62,111]
H4L95 FJI-H5 [194] H4L169 NU-800 [564]
H4L96 [Cu6(OADDI)3(S)6].nS [498] H4L170 NU-1005 [62]
H4L97 ZJNU-77, 78 [499] H4L171 NU-1105 [155]
H4L98 JUC-1000 [500] H4L172 NU-1003 [62] + H4L99 [Zn7(L)3(H2O)7]n [501] H4L173 NU-1004 [62]
H4L100 ZJNU-71 [502] H4L174 NU-1101 [111]
H4L101 ZJNU-74 [502] H4L175 NU-1007 [62]
H4L102 ZJNU-56 [503] H4L176 MFM-133 [565]
H4L103 ZJNU-57 [504] H4L177 C52d-L MOF [566]
H4L104 ZJNU-81–83 [505] H4L178 [Mn2(L)(DMF)(H2O)] 2DMF [147]
(continued on next page) 12 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Table 2 (continued) Table 3 Pentacarboxylate linkers and their corresponding MMCFs. H4L Corresponding MMCFs References H5L Corresponding MMCFs References H4L179 UMCM-313 [68] l H4L180 UTSA-86, PCN-128 W [160,235] H5L1 [Zn6( 3-OH)2(L)2(H2O)6]n [592]
H4L181 [Zn2(tcbpe)] DMA [567,568] H5L2 Ln3(bpbc)(Hbpbc)(H2O)8] [593,594] H4L182 DUT-49 [569] H5L3 [Cu2(L) (H2O)2] [260]
H4L183 Zr(IV)-based Spirof-MOF [227] H5L4 ZJU-72 [595]
H4L184 UPC-21 [141]
H4L185 Zn2(L)(H2O)(DMA) DMA [570] H L186 [Mn L(DMF) (H O) ] [184] 4 2 2 2 2 Table 4 H L187 UHM-25 [230] 4 Hexacarboxylate linkers and their corresponding MMCFs. H4L188 MOF-36, MOF-812, MOF-841 [239,432,571] H L189 PCN-515, JUC-99, [342,572,573] 4 H6L Corresponding MMCFs References H4L190 MOF-33 [432] H6L1 [Cd3(L)(m-H2O)]n [596] H4L191 PCN-521, PCN-523 [574–576] H6L2 MIL-116, UPC-12 [597,598] H4L192 PCN-250 [34] H6L3 [In2(OH)2(H2TTHA)(H2O)2]n [599] H4L193 [Cu2(L3)(DMF)2] [577] H6L4 [Cu6(TTAB)2(l2-OH2)(H2O)8] [133] H4L194 [Cu2(L)(H2O)2], NPF-200 [229,577] H6L5 [[Et2NH2]2[Zn2(L)] C2H5OH]n [185] H4L195 NPF-201 [229] H6L6 UTSA-61 [218] H4L196 [Zn2(X)(CH3CH2OH)] 3H2O [578,579] H6L7 UTSA-20 [42] H4L197 Zn4O(L1)1.5 [102] H6L8 MOF-892, 893, 894 [43] H4L198 Zn4O(L2)1.5 [102] H6L9 Cu6(CTIA)2, ZJU-70 [600] H4L199 Zn4O(L3)1.5 [102] H6L10 rht-MOF-4 [150] H4200 IRMOF-1-L3, SNU-200 [580,581] H6L11 rht-MOF-7 [117,601] H4L201 [Zn2(TPC4A)(DMF)(H2O)4] 3H2O [582] H6L12 [Cu24(TPBTM6-)8(H2O)24]3 [73,118] H4L202 CMOF-1a [583] H L203 CMOF-2a [583] H6L13 Zn-NTTA [124] 4 6 H L204 CMOF-3a [583] H6L14 [Cu3(BTB )]n [164] 4 6 H6L15 [Cu3(TATB )]n [164] H4L205 [Cd2(L)(H2O)2] 6.5DMF 3EtOH [237] H6L16 UOF-2 [341,602] H4L206 UTSA-32 [584,585] H6L17 [Cu3L(H2O)3] xS, SDU-6,7,8 [198] H4L207 CMOF-4a [583] H6L18 NOTT-115 [71] H4L208 CMOF-1 [586] H6L19 PCN-66 [44] H4L209 CMOF-2 [586] H6L20 rht-MOF-6 [72,444] H4L210 MMPF-1 [587] H6L21 NU-138 [220] H4L211 Al2(OH)2TCPP-Co, PCN-222 [588–590] H6L22 NU-139 [220] H4L212 PCN-224(X), X = F, Cl, Br [216] H6L23 NU-125 [76] H4L213 PCN-230 [591] H6L24 NU-140 [220] H4L214 NU-1104–1105 [155] H6L25 PCN-61 [44,603] H4L215 PCN-230 [591] H6L26 NOTT-113, NOTT-114 [71] H4L216 PCN-230 [591] H6L27 NOTT-112 [128]
H6L28 NOTT-111 [77]
H6L29 PCN-69/NOTT-119 [75,78]
[103,104]. The use of multicarboxylate linkers is one straightfor- H6L30 PCN-68, NOTT-116 [70] ward approach to increase the permanent porosity of the obtained H6L31 NU-100, PCN-610 [70,171] architectures [105]. The high porosity of MMCFs can be ascribed to H6L32 NU-109 [108] H L33 NU-110 [108] three key features of multicarboxylate linkers: (1) their versatile 6 H6L34 [Cu(L)1/3(H2O)] 8DMA [604] coordination modes in a range of directions; (2) their large sizes, H6L35 [Cu3(L) (H2O)3]n (solv)x, gea-MOF-2 [57] which increases the distance between metal nodes to form larger H6L36 rht-MOF-9 [74] aperture sizes; and (3) the rigidity of the linker backbone, which H6L37 ZJNU-60 [605–608] prevents frameworks from collapse upon guest removal. H6L38 [Zn7L2(OH)2(H2O)9] [150] H L39 URMOF-1–4 [609] Due to the high stability of the resulting networks, reticular 6 H6L40 UTSA-62a, JUC-100 [45,610] chemistry such as linker elongation is an appealing route to the H6L41 NU-108 [611] augmentation of channel sizes into the mesoporous range H6L42 [Ln(L)0.5(H2O)2] [612] (2–50 nm). Several isoreticular series of tricarboxylate MOFs have H6L43 BUT-46 [613] been reported, such as a series of highly stable Ln-MOFs with H6L44 MODF-1 [614] H6L45 JUC-103, RE-alb-MOF-1 [64,615] tunable luminescence and porosity (Fig. 6) [32]. Furthermore, a H6L46 MFM-112, 132 [616,617] 0 00 mesoporous MOF was constructed with the tricarboxylate 4,4 ,4 - H6L47 Nu-1500 [58] s-triazine-1,3,5-triyltri-p-aminobenzoate (H3TATAB) linker, which H6L48 PCN-136 [618] H6L49 pbz-MOF-1 [619] can be considered as an extension of H3BTC. The resulting frame- H L50 [(CH ) NH ] [(Cd Cl) (TATPT) ] [620] work is isostructural with HKUST-1 [106]. Unfortunately, unlike 6 3 2 2 15 2 3 4 dicarboxylate IR-MOF series, the high structural diversity of tricar- boxylate linkers often prohibits the simple isoreticular expansion of frameworks, as small changes to the linker can have dramatic were constructed with varying linker lengths [107]. The resulting effects on the structure of the framework. MOFs featured high surface areas and facilitated H2 storage capac- When the number of carboxylate groups is increased from three ities due to their large, rigid and aromatic linkers (Fig. 7). In these to four, the effects of linker modification on the framework topol- examples, the sizes of the pores are significantly increased through ogy become less pronounced, as there is less topological variety elongation of the organic linkers, leading to a boost in overall H2 among tetracarboxylate MOFs than tricarboxylate MOFs. This gives adsorption capacity at saturation. However, interpenetration is rise to new opportunities for systematically developing IR-MOF difficult to prevent for structures with long linkers and ultra large series to enhance porosity. For instance, after fabricating MOF- pores, such as NOTT-104 [86]. 0 0 505, an nbo-type MOF based on 3,3 ,5,5 -biphenyl tetracarboxylate Increasing porosity via linker extension has also been well stud- linkers and Cu(II)-paddlewheels, a series of analogue networks ied for MOFs based on hexacarboxylate linkers. For example, the H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 13
Table 5 Octacarboxylate linkers and their corresponding MMCFs.
H8L Corresponding MMCFs References
H8L1 PCN-26 [621]
H8L2 [Cu4L(H2O)4] 2DMF 10H2O [622]
H8L3 UTSA-33, UTSA-34 [623,624]
H8L4 [Cu4(tdhb)] (BUT-155) [136]
H8L5 JUC-118, 119 [46,148]
H8L6 [(CH3)2NH2]4[Cd2(L)] 4H2O [625]
H8L7 [Cu4(L2)(H2O)4] 14DMF 2H2O [626]
H8L8 PCN-922, MFM-180 [91,92]
H8L9 ZJNU-80 [627]
H8L10 [Cu4L1(H2O)4.(solvent)]n [96]
H8L11 [Cu4(L2)(H2O)4] 16DMF 5H2O [628]
H8L12 [Zn4(TDPEPE)-(H2O)4(DEF)4] [93]
H8L13 Cu-tbo-MOF-5 [94]
H8L14 MFM-188 [629]
H8L15 MFM-181 [91]
H8L16 MFM-182 [91]
H8L17 [Cu4(L3)(H2O)3(DMF) (solvent)]n [96]
H8L18 MFM-183 [91]
H8L19 MFM-184 [91]
H8L20 MFM-185 [91] H L21 [Cu [(C H N )(COO) ]] [189] 8 4 57 32 12 8 n Fig. 3. Statistical analysis of the most common topologies for MOFs containing H L22 [(In O) (NO ) (L ) ] [630] 8 3 6 3 6 1 9 planar multicarboxylate ligands according to RCSR. H8L23 NOTT-140 [631]
H8L24 [Zn3(m3-OH)(H2O)]4(L)(L-H2)2 [632]
H8L25 PCN-80 [633]
H8L26 MMPF-2, MMPF-4 [634,635]
H8L27 MMPF-9 [48]
H8L28 UNLPF-2, 10, 13 [636–638]
Table 6 Dodecarboxylate linkers and their corresponding MMCFs.
H12L Corresponding MMCFs References
H12L1 [(CH3)2NH2]6[Cd3L(H2O)2] 12H2O [49]
H12L2 JUC-124 [51,639]
H12L3 In-alb-MOF-1 [50,96]
Fig. 4. Classification of tetratopic linkers based on symmetry, which can be divided
into tetrahedral (Td), square (D4h) and rectangular (D2h). Adapted and reprinted with permission from ref [68].
Fig. 2. Conformations of three classes of tetratopic ligands in MOFs. (a, d)
Conformation of the tetrahedral ligand with D2 symmetry in the flu net framework.
(b, e) Conformation of the rectangular planar ligand with C2h symmetry in the scu net framework. (c, f) Conformation of the rectangular planar ligand with C2v symmetry in the csq net framework. Adapted and reprinted with permission from ref [65]. surface area and pore size of PCN-66 were increased significantly through linker elongation [44]. The enlargement of the (3,24)- connected network topology using a larger hexacarboxylate ligand suggests that the combination of meso-cavities and micro- Fig. 5. Molecular structures of tritopic linkers as longer derivatives of BTC (top). Single crystal structures of MOF-199, PCN-HTB’, and MOF-399 (bottom). Adapted windows could serve as a general approach for constructing stable and reprinted with permission from ref [97]. MOFs with high surface areas. A similar study on hexacarboxylate linkers used in the NOTT framework series showed the same increase in H2 adsorption upon linker extension [107]. These results demonstrate that frameworks assembled from hexacar- pore volumes, and H2 storage capacities (Fig. 8). Generally, hex- boxylate linkers can be easily designed with high surface areas, acarboxylate linkers in combination with paddlewheel clusters lead 14 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Fig. 6. (a-d) Structures of the tritopic organic linkers used in the synthesis of
SUMOF-7I to 7IV (SU = Stockholm University), H3L1 (a), H3L2 (b), H3L3 (c) and
H3L4 (d). (e-h) Crystal structures of SUMOF-7I (e), SUMOF-7II (f), SUMOF-7III (g) and SUMOF7IV (h). The asymmetric unit of SUMOF-7I (i) and the 1D La O chain (j). Adapted and reprinted with permission from ref [32].
Fig. 8. Illustration of hexacarboxylate linkers with various sizes (a) and truncated octahedral cages in their corresponding (3,24)-connected frameworks (b). Adapted and reprinted with permission from ref [107].
0 5 Fig. 9. Chemical structures for the octacarboxylate linkers H8L to H8L used for the synthesis of MFM-180 to MFM-185, representation of the cage assembly in MFM- 180, MFM-181, MFM-182, MFM-183, MFM-184 (*predicted structure) and MFM- Fig. 7. Isophthalate tetracarboxylate linkers and their corresponding Cu(II)-based 185, and corresponding BET surface areas (*computed). Adapted and reprinted with MOFs. Adapted and reprinted with permission from ref [110]. permission from ref [91]. to highly porous and stable rht networks. The NU-110 framework prised of rigid heteropolyaromatic octacarboxylate linkers and has one of the highest experimental BET surface areas reported paddlewheel [Cu2(COO)4] clusters (Fig. 9) [91]. As the linkers were (NU-110, >7000 m2 g 1) and has an rht network topology [108]. elongated, the length of the pores increased, however, the diameter Very recently, the Farha group reported an ultraporous MOF, NU- of the pores remained fixed. The isoreticular design of this series 1501 (Fe and Al), using rigid trigonal prismatic hexacarboxylate resulted not only in systematically increased pore volumes and linker with narrow meso porosity which exhibited pore diameters surface areas for the MOFs upon linker extension, but also higher of less than 2.5 nm. NU-1501 has the highest apparent gravimetric gravimetric and volumetric uptakes of methane. The highly pre- BET surface area among porous materials after satisfying all four dictable self-assembly and tubular pore shapes make this series BET consistency criteria (7310 m2 g 1) [109]. of MOFs a unique platform for further exploring the tunability of The design of IR networks via linker elongation has also been porosity and decoration of pores. studied in octacarboxylate MOFs. For instance, nanotubular pores Although linker elongation may appear a straightforward could be introduced into a series of IR frameworks, which are com- method for increasing the porosity of MOF structures, it typically H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 15
Fig. 10. Three types of pores in an rht framework named as Zn-NTTA. The voids are represented in yellow, violet and royal blue. Adapted and reprinted with permission from ref [124]. increases the likelihood of interpenetration, leading to severe reduction in porosity. Fortunately, interpenetration can be inhib- ited through the use of multicarboxylate linkers due to the topo- logical preferences of MMCF structures. As previously described, MMCFs often generate topological nets that are inherently less prone to interpenetration, such as the nbo, rht and umt topologies reported for NOTT-101, NU-110 and DUT-32, respectively [61,111,112]. The systematic design of MMCFs with these topolo- gies and elongated linkers can lead to MMCFs featuring some of the highest porosities reported for MOFs [108]. Another approach to suppressing interpenetration and improving porosity is the use of asymmetric linkers. In practical MOF synthesis, highly sym- metric linkers are usually preferred as they can facilitate crystal- lization of MOFs and result in more predictable frameworks, while unsymmetrical linkers can lead to formation of MOFs with Fig. 11. Packing diagrams and different types of pores in selected csq-net novel, though often unpredictable, topologies and properties Zirconium MOFs, including hexagonal pores, triangular pores, and windows [39,113]. connecting hexagonal and triangular pores. Adapted and reprinted with permission To fully understand porosity control in MMCFs, different types from ref [62]. of pores within the most common networks must be discussed. The common nbo [114–116], rht [72,117,118], and tbo [94,96,119] topologies possess pores with varying sizes in a single 4. Stability in MMCFs framework, which can decrease the amount of inaccessible space and facilitate mass transfer for guest molecules [120–122]. For When discussing MOFs, stability is broadly defined as resistance example, a tetracarboxylate nbo MOF, ZJNU-50 ([Cu2(L)(H2O)2] of the structure to degradation. Long-term stability under specific 0 6DMF 7H2O; L = 5,5 -(benzene-1,4-diyl-ethyne-1,2-diyl)), exhibits operating conditions is a vital requirement for the application of one of the highest methane working capacities among MOFs due a material. MOFs are often susceptible to heat, humidity, acidic to its two balanced pore sizes [123]. or basic conditions, and guest removal in their target applications The packing of three types of pores in an rht framework with and, as such, stable frameworks must resist degradation under the hexacarboxylate H6NTTA (5,5ʹ,5ʹʹ-((4,4ʹ,4ʹʹ-nitrilotris(benzoyl)) these conditions [129,130]. Due to these requirements, the thermal tris-(azanediyl))triisophthalic acid)) linker is demonstrated in and chemical stability of MOFs has been widely studied. Multicar- Fig. 10. Each of these tetrahedral, octahedral, and cuboctahedral boxylate ligands can be incorporated to construct more robust cavities can be optimized for diverse applications, such as adsorp- MOFs, as the highly connected networks and the diverse coordina- tion and separation [124–126]. The pores can be easily modulated tion modes of the linkers can facilitate the rigidity of the frame- through modification of the linker backbone. Zhou and coworkers works. Chemical stability is mostly attributed to the strength of found that elongation of the hexacarboxylate linker in PCN-61 coordination bonds between the metal nodes and the linkers, as can selectively increase the aperture sizes of the truncated octahe- these bonds can often be readily hydrolyzed, yielding a protonated dral (T-Oh) cages into the mesoporous range without affecting the linker and a hydroxide (or water) ligated node. When multicar- size of the cuboctahedral cavities [127]. NOTT-116, an rht network boxylate linkers are used, the higher connectivity of these linkers with three type of pores, contains a C3 symmetric hexacarboxylate improves stability by increasing the number of M L bonds that ligand and shows a very high BET surface area and total H2 adsorp- must be broken for the linker to be completely hydrolyzed. Addi- tion capacity [128]. tionally, multicarboxylate linkers usually have large backbones 16 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 with extended aromatic skeletons, which increases the hydropho- bic nature of the network and limits the accessibility of the metals to solvent and guest molecules. These features of MMCFs increase the chemical stability of these frameworks. Thermal degradation of MOFs is, in most cases, a result of node–linker bond breakage, accompanied or followed by linker combustion. As a consequence, thermal stability is generally related to node–linker bond strength and the number of linkers connected to each node. Therefore, as with hydrolytic stability, using highly connected multicarboxylate linkers can enhance the thermal stability of MOFs. Another point to mention is that when larger multicarboxylate linkers are used, their consumption may need higher temperature leading to greater thermal stability [131]. Fig. 12. The three organic linkers and network of MUF-77, which features enhanced MMCFs such as MOF-808, MOF-525 and NU-1000 are among moisture stability through ligand design. Adapted and reprinted with permission the most stable frameworks reported to date [132]. The high stabil- from ref [140]. ity of MMCFs further broadens the range of potential applications. For example, NU-1000, a Zr-MOF with a tetracarboxylate linker, and its derivatives have been used in a wide variety of applications of this structure can be ascribed to a combination of two of the due to their exceptional stability. Many IR structures of NU-1000 aforementioned approaches; the H3TTNA linker is fairly hydropho- have also been constructed for specific applications requiring high bic and binds very strongly with the hard, Lewis acidic zirconium stability, such as protein encapsulation (Fig. 11) [62]. High network nodes. Telfer and coworkers focused primarily on the hydrophobic- connectivity also significantly stabilizes the framework of Cu(II) ity approach when developing the MUF-77 series, a set of quater- hexacarboxylate MOFs with large surface areas and high hydrogen nary frameworks with high stability towards water vapor uptake [133]. (Fig. 12) [140]. The crystallinity and porosity of these MOFs are While stability in ambient conditions is important, it is also nec- preserved after exposure to ambient air for 100 days or 20 adsorp- essary to investigate the structural stability of MMCFs under harsh tion–desorption cycles of up to 70% relative humidity. These MOFs conditions. This crucial information provides valuable insight into are stabilized by the rigidity of the linkers and decoration of the tri- structural properties of the frameworks and can guide efforts to carboxylate linker with hydrophobic moieties, which prevents improve the stability of the materials. For example, two MOF mate- water from accessing the labile ZnAO bonds between the cluster V VI rials, NENU-500 ([TBA]3[e-PMo8Mo4 O36(OH)4Zn4][BTB]4/3 18H2O, and the linker. The hydrophobicity of the pore environment can + H3BTB = benzene tribenzoate, TBA = tetrabutylammonium ion) and likewise be improved through extending the aromatic backbones V VI 0 NENU-501 ([TBA]3[e-PMo8Mo4 O37(OH)3Zn4][BPT], H3BPT = [1,1 -bi of organic SBUs. Naphthalene, anthracene and pyrene can be incor- phenyl]-3,40,5-tricarboxylic acid), not only show high stability porated onto multicarboxylate linkers to generate a more towards air, but also feature good tolerance to acidic and basic media hydrophobic structure, resulting in higher stability toward water [134]. This high stability led to their application as the first electro- [144–148]. catalytic MOFs to perform a hydrogen evolution reaction (HER). When considering biological applications, water-stability is perhaps the most important factor for consideration, as most bio- 5. Flexibility in MMCFs logical environments are aqueous [135]. Three main strategies have been used when designing hydrolytically stable MOFs [136]. While recent achievements in construction of MMCFs have led First, hard/soft acid/base (HSAB) theory states that hard, high oxi- to the development of many rigid MOFs with useful properties, dation state metal ions typically form stronger coordination bonds flexible or dynamic MMCFs remain an underdeveloped research with carboxylate ligands than softer, low-valence metal ions. As a field. The relative lack of progress in flexible MMCFs can be attrib- consequence, many highly stable MMCFs containing nodes with uted to difficulties in synthesis, prediction, and control over the hard metal ions, such as Zr(IV), have been designed [137–139]. final networks, however, the unique properties and behaviors of The second approach is to increase the connectivity of the organic these materials have attracted the attention of researchers. Struc- linkers. Many MOFs with highly connected building blocks are tural flexibility can produce dynamic MOFs with unusual proper- hydrolytically robust even when they contain very large pores ties, such as switching or gating behavior derived from a [132]. The third method for improving stability is to increase the conformational change, a ‘‘breathing” ability in the solid state, hydrophobicity of the pore environments by introducing and adaptive recognition for coexisting guests. Many well-known hydrophobic groups onto linkers via direct synthesis or post syn- MOFs are structurally rigid due to their rigid linkers and topologies, thetic modification (PSM) to protect coordination bonds from both of which are common in multicarboxylate MOFs. Flexibility, hydrolysis [36,140]. however, can stem from a range of parameters, such as flexible These approaches are typically straightforward in MMCFs, linkers, variable coordination geometry of the metal ions, interpen- which are often highly connected and can easily be modified to etration, and guest induced movement of the framework [149]. contain diverse linker functionalities. Because of the strength of Because interpenetration is uncommon in MMCFs [150], the pres- the coordination bond between the linker and the metal node, ence of flexible linkers is a key route to generating dynamic MMCFs the central aromatic backbones of the linkers can be easily modi- [151–153]. As discussed in Sections 3 and 4, highly porous struc- fied with different substituents, while the stability and integrity tures may lose their crystallinity upon solvent removal, especially of the frameworks can be maintained [141,142]. when the pore size has been enlarged via linker elongation. Such BUT-13, an MMCF built from zirconium clusters and the tricar- collapse can be prevented by incorporating flexible extended link- boxylate H3TTNA linker (H3TTNA = 6,6ʹ,6ʹʹ-(2,4,6-trimethylben ers into the frameworks, which exhibit reversible breathing behav- zene-1,3,5-triyl)tris(2-naphthoic acid)), has one of the largest sur- ior upon guest removal instead of permanent structural collapse. face areas among water-stable MOFs. Its structure shows no degra- As a result, flexible multicarboxylate linkers are excellent candi- dation across a wide pH range from 2 to 10, which makes it a dates for generating highly connected, stable, soft porous solids promising candidate for antibiotic sensing [143]. The high stability [154]. This approach has been systematically investigated by Hupp H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 17
Fig. 13. Optical photographs of a film based on the [Co3(TBTC)2(DMF)2] 4DMF. The MOF film can serve as a sensor for different organic solvent vapor. Adapted and Fig. 14. Ligand structure and top-down-viewed conformation in crystals of the reprinted with permission from ref [157]. PCN-6X series. and coworkers, who showed that the expanded arms of the during gas adsorption due to free rotation of the CAC and CAN 4 fluorene-based tetracarboxylate linker of NU-1105 underwent bonds of the TCPBDA linker (H4TCPBDA = N,N,N’,N’-tetrakis(4- 0 conformational changes during gas sorption studies [155]. This carboxyphenyl)-biphenyl-4,4 -diamine). Furthermore, the dihedral breathing behavior resulted in a water-stable breathing MOF with angles between the aromatic rings of the linker also change, lead- high surface area. ing to further flexibility across the entire framework [162]. A sim- Separation and sensing studies using flexible MMCFs are preva- ilar route to framework flexibility is through covalent bond lent in the literature. As an example, a flexible bending and curvature change. This was exemplified by the PCN- cyclotriphosphazene-functionalized hexacarboxylate linker was 6X series, in which PCN-69 contains a more bent ligand than its used for preparing the three-dimensional ZJNU-62 ([Pb9(L)3(CH3- analogues PCN-68 and PCN-610 [78]. As a result, PCN-69 is flexible + COO)2(H2O)4]∙2(CH3)2NH2∙12DMA, L = hexakis(4-ethoxycarbonyl- and exhibits gate opening behavior toward gas adsorption, while 3-methoxyphenoxy)cyclotriphosphazene) [156]. ZJNU-62 shows the other two structures do not (Fig. 14). high selectivity towards adsorption of C2 hydrocarbons and CO2 Rigid multicarboxylate linkers can also form flexible frame- over methane at ambient conditions, indicating a promising poten- works by encouraging formation of unique flexible metal clusters. 4 tial for natural gas purification. Cao and coworkers synthesized Min and Choe reported a MOF containing TCPP linkers and unu- m a MOF, [Co3(TBTC)2(DMF)2] 4DMF, based on a flexible ligand 1,3,5- sual [(Zn(COO)3( 2– O)Zn(COO)3] clusters. These clusters act as a tris[4-(carboxyphenyl)oxamethyl]-2,4,6-trimethylbenzene (H3TBTC) hinge, which provides the MOF with a negative Poisson’s ratio. [157]. The MOF can be fabricated into porous films which were The porphyrin linkers form cubes arranged in a distorted body cen- used for sensing and storing the organic vapor of small dye mole- tered cubic structure, however on heating, the cubes pivot around m cules. The ACH2AOA moieties of the linker allow the host frame- the 2–O hinge of the cluster, resulting in dramatic and anisotropic work to change conformation when different guest molecules are thermal expansion [163]. The rigidity of the porphyrin-linked introduced. The cobalt environment is affected by the framework boxes prevents framework collapse upon changing the ZnAOAZn conversion, leading to a color change even at low vapor concentra- angle. tions (Fig. 13). This behavior may be useful in designing optical Functional groups on the linker can also introduce flexibility. As devices based on MOFs. an example, an acylamide-functionalized rht-type flexible MMCF Flexible multicarboxylate linkers have also been known to was reported with high CO2 uptake and selectivity [164].In adopt different conformations and can curl when coordinated to another example, flexibility arose from the ortho-methoxy inorganic SBUs. As a result, aromatic multicarboxylate ligands groups of a 3,3ʹ,5,5ʹ-tetrakis(4-(a-carboxy)methoxyphenyl)-2,2ʹ,6, 0 are suitable linkers for forming helical structures, which are inter- 6ʹ-tetramethoxy-1,1 biphenyl linker, leading to twisted structures esting owing to their relevance to biomolecules such as DNA and and formation of MOFs with different topologies. Generally, proteins. Vishnoi and Murugavel reported a helical structure, [Zn incorporation of tunable functional groups onto the organic linker,
(HL)(H2O)]n (H3L = 2,4,6-tris[(4ʹ-carboxyphenoxy)methyl]-1,3,5-t either at the central core or at the terminal, can lead to distinct rimethylbenzene), which could be obtained through hydrother- MOFs with internal flexibility [165]. mal synthesis [158]. In this structure, the tritopic ligand is doubly deprotonated, with each carboxylate anion bound to a zinc cation 6. Mixed linker MMCFs in a monodentate fashion to form a helical structure. Helical structures are particularly common for frameworks containing An emerging approach to forming highly porous, stable MMCFs tricarboxylate ligands, as the monodentate binding mode of these is employment of mixed linker strategies [166–169]. Mixed-linker linkers are prone to form helices when combined with metal MMCFs (ML-MMCFs) typically exhibit high porosity and stability nodes [159]. and can form unique, non-interpenetrating topologies. While Flexible linkers can also bestow tunable or responsive fluores- mixed linker MOFs containing non-carboxylate-based linkers had cence on a framework. For example, the highly stable PCN-128W been previously studied [170], the first ML-MMCF was reported exhibits unique piezofluorochromic behavior due to changes of by Chen and coworkers in 2003, who utilized both H2BDC and the linker configuration [160]. Similarly, LIFM-66 W undergoes a H3BTC as organic linkers in a three-dimensional zinc-based frame- phase transition to LIFM-66Y upon the application of pressure to work [171]. Since then, several other researchers have used a sim- the (001) face via a scissor-type conformation change of the ilar strategy to design MOFs such as MOF-210, the UMCM-n series, 4 ETTC linker. This transition is accompanied by a cumulative and DUT-32. The high BET surface areas and non-interpenetrating change in fluorescence wavelength [161]. Such compounds with nature of these systems make them highly suitable to applications tunable fluorescence are promising candidates for applications in such as gas storage. These results prove the effectiveness of the photocatalysis and sensing. mixed linker strategy in building ultra-porous non- The introduction of CAC bonds as spacers in multicarboxylate interpenetrating MOFs. linkers can also introduce flexibility into structures in combination In addition to high porosity with limited interpenetration, with dihedral rotations of the linker backbone. For example, the improved stability is one of the most important features of · pores of a flexible In(TCPBDA)(MeNH3) 6H2O framework expanded ML-MMCFs. In 2013, a pair of ML-MMCFs with different mix- 18 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Fig. 15. (a) Tetrahedral cages within MIL-100 and MIL-101. (b, b’) Mesopores within MIL-143. (c) Illustration of the MIL-143 network. (d) Illustration of the b- cristobalite topology. Adapted and reprinted with permission from ref [172]. tures of di- and tricarboxylate linkers, MIL-142 and 143, was reported. These MOFs showed both higher porosity and improved stability compared with their parent single linker sys- tems, MIL-100 and MIL-101 (Fig. 15) [172]. The highly stable MUF-77 reported by the Telfer group also uses a mixed linker Fig. 16. Schematic showing the ligands used in the synthesis of sph-MOFs, (a) strategy to improve stability [140]. As functionalization of the ligands of the spn partial frameworks, the sizes showing distances from the center tritopic truxene-based linker would ordinarily lead to low poros- of linkers to the carboxylic carbon or the center of triazole; (b) ligands of the hxg partial frameworks; (c) structures of sph-MOF-1–4. Adapted and reprinted with ity or dramatic topological changes, a mixed linker strategy was permission from ref [173]. employed to provide a parent structure which was highly toler- ant to modification. The ability to design frameworks with intricate structural com- plexity or unprecedented topologies is another advantage of incor- porating multiple linkers into a single MOF [174,175].An interesting study by the Eddaoudi group demonstrated that highly complex ML-MMCFs with distinct topologies can be obtained by using a merged net strategy [173]. This group showed that by merging two different spn and hxg networks in a one-pot synthe- sis, a complex rare earth-based sph network with both tri- and hexacarboxylate linkers can be synthesized (Fig. 16). Most recently, Zhou, Lan, Qin and coworkers reported two MOFs, PCN-137 and PCN-138, which could be viewed as face-sharing Archimedean solids, which can be generated by using a combina- tion of tri- and tetracarboxylate linkers (Fig. 17) [176]. PCN-137 was comprised of tritopic BTB linkers, tetratopic TCPP linkers and
7-connected Zn4O clusters, in which these components could con- struct a rhombicuboctahedral cage and the square faces of these cages can be fused to generate a qyc network. For PCN-138, the assembly of tritopic TBTB linkers (TBTB = 4,40,400-(2,4,6-trimethyl benzene-1,3,5-triyl)tribenzoate), tetratopic TCPP linkers and 12- Fig. 17. Construction of the two Archimedean face-sharing solids corresponding to connected Zr6 clusters resulted in cuboctahedral cages, which qyc and urr networks. The trit- and tetratopic linker can be simplified as equilateral could be stacked to afford a urr network. This work demonstrates triangles (a) and squares (b) respectively, which can be assembled into cubocta- that the combination of multicarboxylate linkers with different hedron (c) and rhombicuboctahedron (d). 3D networks can be further constructed through stacking of cages (e,f). Adapted and reprinted with permission from ref connectivities and appropriate sizes can generate complicated [176]. frameworks with novel topologies.
7. Synthetic methods in MMCFs tion of unique properties for specific applications. However, less attention has been paid to the development of novel, green, or The last two decades have seen great advances in the field of highly efficient synthetic strategies. To date, most reported MOFs MMCFs, both in the discovery of new structures and the incorpora- have been produced through conventional solvothermal synthesis H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 19
[177], as was used by Yaghi in the synthesis of the first reported MOF [1]. The utilization of new, low-cost synthetic methods for the assembly of MOFs has not been thoroughly studied, making development of synthetic strategies a topic ripe for future research [178,179]. Synthesis of MMCFs is more challenging compared to other MOFs due to the high connectivity of their multicarboxylate linkers [180]. The reaction must be carefully controlled to slow the rate of crystallization. As a consequence, the most common synthetic route of MMCFs is a solvothermal reaction in the presence of a modulator, typically an acid, which can regulate the nucleation rate and control the deprotonation of the linkers [181–183].A range of modulators including nitric acid, hydrochloric acid, formic acid, and acetic acid have been applied in crystallization of MMCFs. A statistical analysis of synthetic methods used in MMCF fabrication shows that mixed solvents are commonly used in the fabrication of MMCFs, as it is one effective method for controlling Fig. 18. Rational percentage of mixed solvent used in synthetic process of all the crystallization process (Fig. 18). [141,182,184] Although the MMCFs listed in this review. exact reason for improved crystallization in mixed solvents remains unclear, it may be attributed to differing solubilities of the linkers and the metal salts in various solvents. Multicarboxy- late linkers are typically large and aromatic, resulting in poor sol- ubility in polar solvents, while the metal salts, as precursors for metal clusters, are poorly soluble in most organic solvents. Consid- ering the requirement for coordinating solvents with high boiling points in MOF synthesis, the range of single solvent systems which can be used to prepare MMCFs is severely restricted. In addition, a report by Hong and coworkers demonstrated that altering the composition of a ternary mixed solvent used during the synthetic process can influence the coordination modes of the ligand, result- ing in the formation of different frameworks [185]. This demon- Fig. 19. Proposed energy diagram of different reaction pathways for dual exchange strates that judicious choice of solvent can not only modulate the in PCN-333. Adapted and reprinted with permission from ref [33]. crystallization of MMCFs, but also tune the features of the as- synthesized frameworks. Unfortunately, the high connectivity of multicarboxylate linkers As the complexity of MMCFs increases, it becomes more chal- means it is usually unfavorable to perform PSM techniques such as lenging to construct MMCFs through one-pot synthesis, as the linker exchange in MMCFs. While linker or metal exchange is diffi- building units of the framework may not be stable enough to sur- cult to realize in MMCFs, it is more facile to perform PSM without vive solvothermal synthesis [186]. In these situations, PSM has interrupting the bond between the metal and the carboxylate become an increasingly attractive alternative to one-pot synthesis. group. One method by which this can be achieved is post- The topology and functionality of as-synthesized MOFs can be judi- synthetic metalation of the cluster. NU-1200, a tricarboxylate ciously modified by post-synthetic alteration of both the metal Zr-based MOF, has an open and easily modifiable network. The cluster and the organic moieties [187]. Zr cluster of this structure can be post-synthetically metalated PSM is especially useful when the target framework contains with a reactive Ti4+ species [188]. Alternatively, the linker can be building units that are incompatible with the synthetic conditions modified by the addition or alteration of functional groups. For required to generate the framework [186]. The Zhou group demon- example, UHM-8, a structure containing a tetracarboxylate linker strated the versatility of this method in the preparation of (5,5ʹ-(1,4-phenylenedi-2,1-ethinyl)-bis(1,3-benzenedicarboxylic azide-functionalized N3-PCN-333(Cr). This structure is not directly acid) and Cu nodes, could be quantitatively brominated, demon- accessible via solvothermal synthesis, as hydrothermal synthesis is strating the first modification of a nonterminal triple bond within typically required for Cr-MOFs, the TATB ligand is poorly soluble in a MOF [123]. Although several striking examples of PSM have been water, and the complex geometry of azide-functionalized TATB is reported in MMCFs, this area has not been explored in great depth less compatible with the desired framework architecture. How- and can create new possibilities for future research. ever, non-functionalized PCN-333(Fe) is readily accessible via solvothermal synthesis and the Fe(III)AO bond between the cluster and the linker is labile enough to allow linker exchange between 8. Functionality in MMCFs TATB and its derivatives. Post-synthetic substitution of the Fe atoms for Cr and azide-functionalization of the linker could be per- Although porosity is perhaps the most commonly discussed formed to generate N3-PCN-333(Cr), which is more stable than the property of MOFs, the ability to introduce a variety of additional parent structure. Linker exchange in the post-synthetically modi- functionalities is one of the greatest advantages of MOFs over other fied structure is prohibited, as the Cr(III)AO bonds are much more porous materials. Conventional porous materials such as zeolites robust than the Fe(III)AO bonds of the parent structure, with the and activated carbons typically lack highly tunable organic moi- energy barrier for linker dissociation prohibitively high (Fig. 19). eties or feature small cavities with disordered functional groups. Furthermore, the azide functionalized linker is a useful platform In contrast to these materials, MOFs possess a high degree of tun- for further functionalization through click chemistry. This work ability due to the versatility of the organic linkers and the highly presented a detour strategy for dual exchange in a robust frame- ordered nature of their pores. The organic linkers can be elabo- work, which provided a unique perspective for PSM in MMCFs [33]. rately designed to tune the properties of the frameworks. As a 20 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 result, the acidity, polarity, size, and hydrophobicity of functional- ities incorporated into linkers are all important factors for advanced efficiency in applications [189,190]. In applications requiring the presence of multiple functional groups, a key challenge is the propensity of the functional groups to interact with each other, which can have a deactivating effect on the desired dual functionality or synergistic effect. The incorpo- ration of these functional groups in framework materials can pre- vent this phenomenon and improve the host–guest interactions within the pores. When designing multifunctional materials, MMCFs are often superior to other MOFs, as their highly connected linkers can tolerate the pre- or post-synthetic incorporation of a wide range of functionalities without collapse of the internal cavities. The introduction of multiple functional groups in a single net- work can be a route to enhancing the adsorption behavior of the resulting MOF [191]. For example, the dual functionalities stem- 0 ming from the isophthalate and triazole moieties in the 5,5 -(1H- Fig. 20. H3BTB linkers functionalized with various function groups at selected 1,2,4-triazole-3,5-diyl) diisophthalic acid linker of JLU-Liu20 lead positions and corresponding MOFs formed either by pure linker or various linkers. H BTB (A); H BTB-NH (B); H BTB-NO (C); H BTB-OCH (D); H BTB-OC H (E); to a framework with high surface areas, multiple pore environ- 3 3 2 3 2 3 3 3 7 7 H3BTB-(F)2 (F); H3BTB-C4H4 (G); H3BTB-F (H); H3BTB-CH3 (I); H3BTB-m-NH2 (J); ments and high density of open metal sites [192]. Another similar H3BTB-C4H4/NH2 (K). Adapted and reprinted with permission from ref [63]. report showed the existence of dual functionalities in ZJNU-54, which was among the best performing materials for C2H2 and CO2 adsorption in the literature [193]. In this framework, three dif- ferent pore environments exist within the structure. Each pore was variously decorated with open metal sites and uncoordinated amine and pyridyl nitrogen sites, which allowed the MOF to effec- tively capture multiple gases. Another report discussed the synthe- sis of a highly porous MOF with an extended, semi-rigid, bent diisophthalate ligand. The structure contains three types of polyhe- dral pores and two types of one-dimensional channels. The two unique pore environments are characterized by the alignment and orientation of the open copper sites and linkers to achieve high
H2 and CH4 uptake [194]. These works demonstrate the role of MMCFs as ideal prototypes to achieve synergy between functional groups while preserving the crystallinity and porosity of the frameworks. Introducing functional groups into multicarboxylate linkers can lead to topological differences in the target structures of MMCFs. A study by Yaghi and coworkers on the MOF-177 series indicated that the introduction of functionalities in different positions around a tritopic H3BTB linker could change the framework topol- ogy from qom to pyr or rtl (Fig. 20) [63]. The qom topology has lower symmetry in comparison to pyr and rtl and shows ultrahigh porosity and gas uptake. The substitution of different functionali- Fig. 21. RE-MOFs with diverse topologies can be generated through tuning the ties on a tetracarboxylate linker has also drastically impacted the steric hindrance of a functionalized tritopic linker. Adapted and reprinted with structure and gas adsorption properties of ZJNU-55 and led to permission from ref [80]. the discovery of a new topology in the resulting nets [195]. Most recently, Zhou, Sun and coworkers reported that incorporation of groups into the tetracarboxylate linker of ZJU-130 led to the forma- various functional groups onto the central phenyl ring of a tritopic tion of non-interpenetrated ZJU-31, which possessed a higher BET linker [1,1:3,1-terphenyl]-4,4,5-tricarboxylic acid could result in surface area than ZJU-130, an interpenetrated framework (Fig. 22) RE-MOFs with different topologies [80]. Introducing bulky func- [197]. Functional groups can also affect the overall properties of tional groups such as ANH2, ACH3 and ACl restricted the rotation of the lateral phenyl rings, leading to an sep network, while less MMCFs such as hydrophobicity and stability [198,199]. The stabil- ity of MMCFs can be tuned by incorporating a variety of functional bulky function groups like AH, AF and AOCH3 led to the formation of a novel ytw network. Interestingly, the combination of two dif- groups. A report by Zhou and coworkers showed that upon the ferent linkers with bulky and less bulky function groups resulted in introduction of a ligand containing a triazine functionality, the sta- · + · · a network with an unprecedented flg topology (Fig. 21). This work bility of the MOF [M6O(TATB)4 (H )2 (H2O)n (Py)] (M = Co, Zn, Mn, ʹ ʹʹ demonstrated that the steric hinderance of functional groups can Py = pyridine, TATB = 4,4 ,4 -s-triazine-2,4,6,-triyl-tribenzoate) tune the configurations of multicarboxylate linkers and lead to was improved due to the planarity of the linker, which was the discovery of frameworks with novel topologies. allowed more favorable p-p interactions [200]. Moreover, another By introducing bulky function groups into MMCFs, interpenetra- report showed that introducing hydrophobic moieties into linkers tion can be inhibited even when the linkers are lengthened. For can prevent the water molecules from attacking the metal nodes instance, MFM-130 and MFM-131 afforded non-interpenetrated and improve the stability of MOFs [201]. Therefore, linker design structures, which were synthesized via extra-long linear tetracar- is a necessary pathway to construct MMCFs with specific boxylate linkers [196]. In another study, incorporation of methoxy properties. H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 21
Fig. 22. Incorporation of -OMe group resulting in non-interpenetrated ZJU-31 with higher BET surface area. Adapted and reprinted with permission from ref [197].
The functional groups can be judiciously oriented in the pore Fig. 23. Selected MOFs comprised of tetratopic linkers and paddle-wheel [Cu environment of MMCFs, improving their ability to interact with 2 (COO)4] clusters, termed as NOTT-101 (grey), ZJU-5 (green), UTSA-75 (yellow), and guests [202,203]. For example, large cavities together with judi- UTSA-76 (red). Spheres represent voids within the MOFs. Adapted and reprinted ciously positioned acylamide groups in an rht-type Zn-NTTA with permission from ref [207]. framework made the catalytic sites of the framework readily acces- sible for encapsulated substrates [124]. Enhanced carbon dioxide SBUs are usually constructed in different ways, with clusters often capture and chemical fixation were observed in this MOF without formed in situ and linkers either pre- or post-synthesized. The the need for further separation and purification. A similar principle rational design of the linker generally dictates the structure of can be observed in a polar ketone functionalized Cu-MOF-1, which the resulting MOF. Various linker modification strategies such as contains two distinct pore environments. The uncoordinated car- linker extension, introduction of additional functionalities, modifi- bonyl groups of the ketone functionality were oriented toward cation of the flexibility, and alteration of the symmetry can be its rhombicuboctahedral cages, and led to its high performance easily applied to multicarboxylate linkers, providing chemists in gas adsorption [204]. Another study on three isostructural opportunities to rationally tailor MMCFs to optimize their perfor- MMCFs (denoted as NOTT-113, NOTT-114 and NOTT-115) with dif- mance in specific applications. When considering applications, ferent functionalities on the central core of their hexacarboxylate high porosity and stability are two of the most important proper- ligands showed that functionalization of the cage walls with more ties of MMCFs. Incorporating multicarboxylate linkers can improve aromatic rings could increase the strength of H2/framework inter- these two properties due to the high connectivity and versatile actions. Furthermore, measurement of Qst revealed that the amine coordination modes of the linkers. group in the core of the NOTT-114 ligand gave a notably lower H2/ HKUST-1, one of the most well-studied MMCFs, contains a sim- framework binding energy [71]. ple tritopic H3BTC linker and has attracted substantial attention The basicity of the pore environment is another important owing to its high potential in various experimental and industrial structural property which can directly affect the host–guest inter- applications [30]. The design of more complex linkers with a actions and improve guest uptake efficiency [205]. In MMCFs, sim- similar geometry to H3BTC and the subsequent construction of ple modification of functional groups can improve this parameter. HKUST-1-like MOFs have led to great advances in MMCFs [209]. For example, decoration of highly porous rht-type MOFs with hex- Furthermore, by increasing the number of coordinating carboxy- acarboxylate ligands and polar acylamide groups could signifi- late groups in MOFs, novel topologies and structures, such as cantly enhance the CO2 binding and selectivity of MOFs NOTT-105/110/111 [86,210], PCN-46/69 [78,89], NU-125 [76], [117,118]. In another example, a high density of Lewis basic nitro- UMCM-151 [39], and UTSA-60/88 [211,212], can be developed gen sites in ZJU-40a ([Cu2L(H2O)2] 7DMF 4H2O) resulted in the sec- and new opportunities for using MOFs in a wide range of applica- ond highest C2H2 uptake according to the literature [206]. tions have recently been explored (Fig. 24). Similarly, Lewis basic nitrogen sites could be incorporated into Fig. 25 summarizes the most-reported applications of MOFs and the pores of NOTT-101 through installing pyridine, pyridazine, their prevalence in MMCF research. As shown, gas adsorption and pyrimidine functionalities in the organic linkers, which [213], sensing [214,215] and catalysis [216] are the most widely significantly improved the volumetric methane storage and studied applications of MMCFs in the literature. This arises from working capacity (Fig. 23) [207]. This work is expected to motivate the suitable porosity [171], rigidity [91] and stability [138] of more extensive research to develop new MOFs containing diverse MMCFs, which can be attributed to highly connected linkers functional groups to target higher methane storage and working together with unsaturated metal sites. capacities in the near future.
9.1. Gas storage and separations 9. Applications of MMCFs MMCFs are among the best candidates for gas adsorption and The most important feature of any MOF is its performance have some of the highest surface areas in the MOF field towards a target application, which is directly affected by the [108,166,217]. The use of multicarboxylate linkers can direct the metal clusters and organic linkers of the structure [208]. These network topologies and endow the MOF with suitable pore envi- 22 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Fig. 24. Summary of a statistical analysis of MMCFs applications. Fig. 25. Functionalization of pyrazine into backbone of tetratopic linkers trans- ronments. As previously mentioned, the nbo and rht topologies forming NOTT-101 to ZJU-40. Spheres represent internal cavities within MOFs. commonly generated by tetra- and hexacarboxylate linkers can Adapted and reprinted with permission from ref [206]. provide different types of pores and open metal sites, which can affect the adsorption properties of these MMCFs. Many nbo type
MMCFs feature high H2 affinity due to presence of open metal sites, while rht type MMCFs typically show better affinity to other gas molecules such as methane due to their appropriate pore dimen- sions [107]. For instance, UTSA-61 ([Cu3L(H2O)2.5], L = 1,3,5-tris(3, 5-di(4-carboxyphenyl)phenyl)benzene), a MOF containing a short- ened hexacarboxylate linker of C2 symmetry, featured both high vol- umetric methane storage and working capacities, rendering it as a promising adsorbent for on-board methane storage [218].Another
MMCF, ZJU-40 ([Cu2L(H2O)2] 7DMF 4H2O, H4L=5,5ʹ-(pyrazine-2,5- diyl)diisophthalic acid), which is isostructural with NOTT-101, fea- Fig. 26. The NU-138, NU-139, and NU-140 comprised of hexacarboxylic linkers and paddle-wheel [Cu2(COO)4] clusters as methane adsorbent. Adapted and reprinted tures the second-highest gravimetric C2H2 uptake among all with permission from ref [220]. reported MOFs due to the Lewis basic nitrogen sites of its linkers (Fig. 25) [206]. Interestingly, these immobilized nitrogen sites have nearly no effect on the CO2 uptake, making ZJU-40 a good material for highly selective C2H2/CO2 separation. In another similar work, ciency as heterogeneous catalysts or supports for single site incorporation of a linker with a polarized heteroaromatic ring catalysts in a range of catalytic systems [222–224]. By using mul- ʹ (5,5 -benzo[c][1,2,5]thiadiazole-4,7-diyldiisophthalic acid) to form ticarboxylate linkers instead of ditopic linkers, the topologies of the the MOF ZJNU-40 also leads to improved CO2 gas sorption and selec- resulting frameworks can be tuned directly, which further tailors tivity compared to NOTT-101 [219]. the pore environment to enhance the catalytic activity. For As previously discussed, the coordination modes of multicar- example, it was reported by Hupp’s and Farha’s groups that the boxylate linkers and the topologies of resulted networks inhibit pore apertures of UiO-66, a MOF with ditopic linkers, are too small net interpenetration. This property promotes the formation of for the hydrolysis of chemical warfare agents. As a result, the sorp- frameworks with high porosity and better performance in gas tion capacity and resulting hydrolysis activity were restricted to adsorption. For example, Zhou and coworkers reported that a sites on the exterior surface of the MOF crystallites. However, framework extended in a (3,24) network with hexacarboxylate through using NU-1000, improved hydrolysis behavior was linkers, was highly porous with near record-high surface areas observed due to the formation of ultrawide channels generated and no interpenetration [70]. by an extended tetratopic linker. This improved the accessibility Another advantage of multicarboxylate linkers is that straight- of the Lewis-acidic Zr(IV) nodes inside the pores, which behave forward extension of the central aromatic rings can form novel IR as the catalytically active sites [225]. MMCFs with enlarged pore sizes and optimized properties [88]. Another report by Farha and coworkers indicated that a flexible For instance, a series of hexacarboxylic acid linkers of different Zr-MOF with a tetratopic linker, NU-1400, featured guest and sizes can form various isoreticular (3,24)-connected MOFs (NU- temperature-dependent structural dynamics. This structure can 138, NU-139, and NU-140) [220]. Incorporation of additional aro- be used for shape selective/switchable catalysis due to the reduced matic rings into the central backbone of the linker of NU-140 leads connectivity of its metal nodes and linkers, which allows for higher to greater structural integrity during activation, a high BET surface degrees of freedom and leads to variable pore sizes. [226] In 2 area of 4300 m /g, and improved methane adsorption (Fig. 26). In a another case, a Zr(IV)-based Spirof-MOF with a tetracarboxylate similar study, extending the backbones of tricarboxylate ligands linker acted as an active material for the effective hydrolysis of · via click chemistry leads to a highly porous MOF Zn6(L1)4 (H2O)3 nerve agents and their simulants [227]. Telfer and coworkers ʹ ʹʹ (L1 = 4,4 ,4 -benzene-1,3,5-tryl-tri(1H-1,2,3-triazol-1-yl)benzoic demonstrated that multicomponent frameworks are a powerful acid) with large pores, leading to good adsorption of large guest new class of heterogeneous catalysts in which modulator groups molecules [221]. could be positioned in the pore to influence the catalysis [228]. In this work, three ligands with different geometries (one tritopic 9.2. Catalysis and two ditopic) were utilized to control the apportionment of dif- ferent steric modulators for catalysis in MUF-77. This shows the In addition to gas adsorption, an increasing number of investi- importance of linker geometry and MOF topology to the precise gations on the catalytic performance of MMCFs confirm their effi- design of catalysis within MOFs. H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 23
Besides the effect of linker topicity on pore environment and areas. The high uptake in water adsorption of MMCFs can be attrib- catalytic performance, the multicarboxylate ligand can not only uted to the large and hydrolytically stable pores of these frame- act as a support for a metal catalyst, but also ensure high stability works. Yaghi and coworkers compared the water adsorption of the framework through high connectivity and strong properties of 23 materials and found that MOF-841, which con- coordination bonds. Reports on porphyrinic MOFs such as tains tetracarboxylate ligands and Zr6 clusters, featured the best PCN-22/222/224 from the Zhou group demonstrated that these behavior in water adsorption (44% water uptake at P/P0 = 0.3). structures displayed high stability owing to the high connectivity MOF-841 has potential to be used in the capture and release of of the TCPP linkers and strong bonding between carboxylate and atmospheric water in remote desert areas [239]. The water sorp- high-valent metals. For instance, PCN-224 can efficiently catalyze tion properties of MIL-100(Fe and Al) has been investigated by
CO2/propylene oxide coupling while preserving the integrity and Janiak et al. These structures show very promising, high water crystallinity of the MOF after catalysis [216]. capacities, very good cycle stabilities, suitable hydrophilicities Similarly, two Zr-MOFs, NPF-200 and NPF-201, were fabricated and little hysteresis which make them suitable candidates for using tetrahedral linkers and Zr clusters [229]. NPF-201 was used thermally driven heat pumps or adsorption chillers [240]. Later as a catalyst and exhibited highly selective uptake of photoac- developments by Eddaoudi and coworkers demonstrated that 2+ tive [Ru(bpy)3] (bpy = bipyridine) for the heterogeneous Cr-soc-MOF-1, a Cr(III)-MOF based on a tetratopic ligand, featured photo-oxidation of thioanisole. In another report, NENU-500 an apparent surface area of 4549 m2/g and showed the highest V VI ([TBA]3[e-PMo8Mo4 O36(OH)4Zn4][C24H15(COO)3]4/3 18H2O) and water adsorption capacity among all water vapor adsorbents V VI NENU-501 ([TBA]3[e-PMo8Mo4 O37(OH)3Zn4][BPT]) with tricarboxy- reported to date [241]. These works demonstrate that high- late H3BTB ligands were used to perform a hydrogen evolution reac- valent metals like Zr(IV) and Cr(III) and large apertures are neces- tion (HER) for the first time, achieving record performance among sary features for MOF-based water adsorbents, while the high con- MOF materials [134]. Additionally, the UHM-25 series, MOFs based nectivity of multicarboxylate linkers can enhance the framework upon [Cu2(COO)4] paddle-wheel clusters and a chiral tetrocarboxy- stability during water capture. Another report was done by Farha late linker, can be used as heterogeneous, stereoselective catalysts group on water adsorption in NU-1500-Cr, which is based on triva- in the aldol addition reaction of acetaldehyde [230]. These reports lent trinuclear metal clusters and a rigid trigonal prismatic hex- further confirm that the incorporation of highly connected linkers acarboxylate ligand. The highly porous and hydrolytically stable can enhance the stability of MMCFs and facilitate their catalytic NU-1500-Cr can be activated directly from water and displays an behavior. impressive water vapor uptake with small hysteresis [58]. A simi- lar study investigated water adsorption of three porphyrin based 9.3. Sensing MOFs, which showed promising water adsorption–desorption capabilities. The adsorption mechanism of water onto these por- As displayed in Fig. 25, the application of MMCFs as sensing phyrin based MOFs demonstrated that the water strongly interacts materials has been widely studied alongside gas adsorption and with the whole structure, and adsorption is not limited to the catalytic applications. Most of these investigations focus on detect- metal node [242]. The tetracarboxylate RE-MOF Y-shp-MOF-5 has ing heavy metal ions and organic species like aromatic molecules also been reported and acts as an ideal adsorbent for humidity- for water purification [231]. For optimized sensing of organic guest triggered water capture and release systems for adsorption-based molecules, a highly selective and robust framework with an moisture controlled processes [243]. electron-rich backbone is required, along with a hydrophobic pore environment [230,232]. Appropriate functionalities, such as acids, 9.5. Biological applications amines, hydroxyl groups and N-containing heterocycles, are also required for heavy metal sensing [233–236]. MMCFs are promising In addition to water adsorption, the biological applications of materials as sensors because a range of properties can be judi- MOFs have generated a flurry of interest in recent years ciously incorporated into the structure, such as high stability and [143,244]. Although there are few examples of MMCFs with being rigidity, tunable interpenetration, different pore sizes, and used for biological applications in the literature, these frameworks straightforward incorporation of function groups. For instance, a are promising candidates for such studies due to their high stabil- chiral porous MOF [Cd2(L)(H2O)2] 6.5DMF 3EtOH (L = (R)-2,2ʹ- ity, porosity, tunable functionality and accessible coordination dihydroxy-1,1ʹ-binaphthyl-4,4ʹ,6,6ʹ-tetrakis(4-benzoic acid)) can sites [245,246]. For instance, the high water stability, act as an enantioselective fluorescence sensor for amino alcohols multi-functionality, large surface area, and specific electrochemical
[237]. Interactions between the amino alcohol guest and the aro- properties of MOF-515 ([[Al3(l3-O)(NTB)2(H2O)3](NO3)(NMF)10 0 0 matic binaphthol moieties of the linker resulted in greatly (H2O)7.5], H3NTB = 4,4 ,4 ’-nitrilotribenzoic acid) and MOF-516 enhanced sensitivity and enantioselectivity over the corresponding ([Al4(OH)4(H2O)(NTB)2(HCOO)3](HCOO)(NMF)14.5(H2O)4]), which homogeneous systems. Another striking report showed the capa- are based on tricarboxylate linkers (Fig. 27), make them promising bility of a novel Zr-based MOF with a tetracarboxylate ligand biosensors, especially when combined with antibodies [247]. This (1,3,6,8-tetra(4-carboxybiphenyl))pyrene) to sensitively detect study demonstrates potential applications for MMCFs in environ- and sequester nitrobenzene (NB) [238]. The pyrene core of the mental protection and food safety. ligand was strongly fluorescent and had a strong fluorescence MOFs are also promising platforms for the encapsulation of bio- quenching effect towards encapsulation of NB. In addition to sens- molecules such as enzymes and drug molecules to construct a ing, the MOF can also capture NB with a high capacity. In principle, composite material. In general, the immobilization of biomolecules the combination of fluorescent groups and porosity can result in in MOFs can be achieved via four different methods, namely sur- MMCFs with high sensitivity towards guest molecules. face attachment, covalent linkage, pore encapsulation and co- precipitation [248,249]. Covalent linkage is mostly reported in 9.4. Water adsorption MOFs with ditopic linkers, while co-precipitation is a method widely applied in zeolitic imidazolate frameworks. In the case of Water adsorption, which is a new important application for surface attachment, enzymes can be anchored onto the MOF sur- MOFs, has also been studied in MMCFs. Water adsorption in porous faces directly through weak, noncovalent interactions. As a result materials is important for many applications such as dehumidifica- of the non-specific nature of these interactions, the surface attach- tion, thermal batteries, and delivery of drinking water in remote ment method can be applied in a broad range of MOFs and 24 H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542
Fig. 28. (a) Size-selected encapsulation of insulin within NU-1000. (b) The selective Fig. 27. Electrochemical biosensor fabricated through Al-based 515- and 516- release of insulin from NU-1000 in PBS solution. Adapted and reprinted with MOFs. Preparation of Al-MOFs based on Al (i), adsorption of antibody (ii), and permission from ref [259]. detection of antigen (iii). Adapted and reprinted with permission from ref [247]. enzymes, including MMCFs. For instance, Steunou, Legrand and co- workers utilized the nanocomposites of platinum nanoparticles exist in the framework, leading to strong supramolecular interac- and MIL-100(Fe) with tritopic linkers as the immobilization matri- tions, specifically hydrogen bonds, with guest molecules. These ces of glucose oxidase. The MIL-100(Fe) composite featured a high diverse interactions within the framework can contribute to con- biocompatibility and the composite material can serve as a ductivity and sensing behaviors of the MMCF. For example, the bio-sensor for glucose detection [250]. Liu and co-workers also hexacarboxylate linker H6CPB (1ʹ,2ʹ,3ʹ,4ʹ,5ʹ,6ʹ-hexakis(4-carboxy reported the immobilization of Bacillus subtilis lipase onto phenyl)-benzene) can retain two free carboxylate groups upon HKUST-1 through surface attachment [251]. Owing to the high forming a Zr-MOF [43]. The free carboxylates of the linker can work connectivity of multicarboxylate linkers, large and robust pores in tandem with the acidic Zr clusters to promote catalytic CO2 can be constructed within MMCFs, making the pore encapsulation cycloaddition. The presence of coordinatively unsaturated metal an efficient approach for enzyme immobilization. For example, sites and exposed ACOO groups in the nbo type framework of PCN-333, an mtn-type MOF based on tritopic linkers and 0 0 [Cu2(L) (H2O)2] 2H2O 3DMA (CH3)2NH2 (L = 2,5-bis(3 ,5 -dicarboyl trimeric-oxo clusters, has large internal cavities to trap enzymes phenyl)-benzoate) may contribute to its selective CO2/N2 adsorp- [252]. The encapsulation can boost the catalytic performance of tion and dye separation [260]. In another work, Zima and cowork- the enzyme compared to free enzymes. Through elaborate exten- ers reported that free carboxylate groups within LiTFTA sion of the tritopic linker, the size of the pores can be further ([Li6(C8H5O9)2(H2O)3] 3H2O) pores made a 3D network with exten- enlarged, allowing for immobilization of enzymes with various sive H-bonds which are responsible for the protonic conductivity sizes [253,254]. The MOF-enzyme composites can resist trypsin of this compound in humid conditions [261]. In addition to the digestion and produce anti-cancer molecules in a long-lasting fash- aforementioned study, the free carboxylate groups of the tricar- ion. One essential parameter in the pore encapsulation is compat- boxylate H3OABDC (5-oxyacetateisophthailic acid) linker in the ibility of the sizes of MOF pores and the enzymes [255]. For [Cd3(OABDC)2(H2O)5] 2H2O framework could be partially or fully instance, a Zr-MOF with tetratopic linkers, PCN-128y, featured deprotonated to serve as hydrogen bond donors or acceptors, lead- mesoporous channels at 4.4 nm, whose sizes allowed the confine- ing to higher dimensionality of the complex to form a 3D frame- ment of organophosphorus acid anhydrolase, leading to a 12 wt% work [262]. loading capacity [256]. It should be noted that MMCFs can be One other significant feature of MMCFs is the presence of designed to degrade under specific conditions and the sizes of extended aromatic ring systems which can form p-p stacking and MOF particles can be finely controlled through synthetic tech- aromatic CH-p interactions with guests to improve the adsorption, niques. This makes them promising candidates for drug delivery separation and sensing ability of the structures [264–266]. An excit- and imaging [257]. For instance, Zhou, Mao and coworkers ing example demonstrated that the hydrogen bonding, p-p stacking, reported precise size control of nano-sized porphyrin MOF PCN- and intermolecular dipole interactions in NOTT-300 can form weak 224 in a bottom-up manner [258]. Nanoscale PCN-224 could serve supramolecular interactions with the unsaturated hydrocarbons as a platform for targeted photodynamic therapy. In 2018, Farha acetylene and ethylene [267]. The fine tunability of these interac- and coworkers incorporated insulin into an acid-resistant tetracar- tions results in optimal uptake kinetics and binding dynamics to give boxylate MOF, NU-1000, to construct a composite to combat dia- outstanding selectivity between these two hydrocarbons. In another betes [259]. The mesopores of NU-1000 prevented the entrance report, CTGU-7 ([NaEu2(TATAB)2(DMF)3] OH (H3TATAB = 4,4ʹ,4ʹʹ- of pepsin into the framework, while the framework was preserved s-triazine-1,3,5-triyltri-m-aminobenzoic acid), which contains an even in stomach acid. When the insulin@NU-1000 composite was aromatic tricarboxylate linker, was the first MOF used for the selec- exposed to phosphate-buffered saline (PBS) solution, a condition tive detection of ornidazole antibiotics due to its high sensitivity for mimicking the bloodstream environment, the framework nitrophenol and benzyl alcohol moieties [268]. This material can degraded, releasing insulin (Fig. 28). potentially be used as a multi-responsive luminescent sensor due to the presence of p-p and CH-p interactions in tandem with its 9.6. Other features of MMCFs rare-earth metal nodes. Additionally, the use of multi-aromatic hydrocarbon units as the core of linkers can lead to the design of Multicarboxylate linkers can adopt versatile coordination hydrophobic MOFs for oil/water separation [263]. UPC-21, con- modes to metal nodes. This feature allows free COO moieties to structed from a pentiptycene-based organic ligand with extended H. Ghasempour et al. / Coordination Chemistry Reviews 426 (2021) 213542 25
ing applications, including drug delivery, chemical sensing, selective separation and sequestration of pollutants. Overall, as a perspective, this review summarizes the advantages of using mul- ticarboxylate linkers within MOF structures, demonstrating that they are a powerful tool for the design of advanced materials with superior stability, porosity and applicability. Additionally, using compatible multicarboxylate linkers with appropriate metal nodes can offer new horizons for MOF scientists to develop novel net- works and overcome obstacles in MOF synthesis.
Declaration of Competing Interest
The authors declare that they have no known competing finan- cial interests or personal relationships that could have appeared to influence the work reported in this paper.
Acknowledgment
Support of this investigation by Tarbiat Modares University is gratefully acknowledged. This work was supported by the Center
Fig. 29. Separation of water/oil through UPC-21 crystals, in which water was for Gas Separations, an Energy Frontier Research Center funded colored with acid red 18. Adapted and reprinted with permission from ref [263]. by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DE-SC0001015, the Robert A. Welch Foundation through a Welch Endowed Chair to HJZ (A- aromaticity in its central rings, was the first reported highly 0030), U.S. Department of Energy Office of Fossil Energy, National hydrophobic MOF for efficient oil/water separation (Fig. 29). In Energy Technology Laboratory (DE-FE0026472) and National another study, the tetracarboxylate linker TBAPy (1,3,6,8-tetrakis Science Foundation Small Business Innovation Research (NSF- (p-benzoic acid)pyrene), with a long-lifetime fluorescent core, can SBIR) under Grant No. 1632486. be used to construct a 3D MOF ([In2(OH)2(TBAPy)]) and form p-p stacking interactions with nonpolar guest molecules, leading to a Appendix A. Supplementary data high fluorescence sensitivity to guest molecules. Notably, the quan- tum yield and microsecond lifetime of this framework are similar to Supplementary data to this article can be found online at those of Eu(III)-cryptate based commercial sensors [269]. 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