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Three Novel Zn-Based Coordination Polymers: Synthesis, Structure, and Effective Detection of Al3+ − and S2 Ions

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Three Novel Zn-Based Coordination Polymers: Synthesis, Structure, and Effective Detection of Al3+ − and S2 Ions molecules Article Three Novel Zn-Based Coordination Polymers: Synthesis, Structure, and Effective Detection of Al3+ − and S2 Ions 1,2, 1,2, 1,2 1,2 1,2 1,2 Yuna Wang y, Xiaofeng Zhang y, Yanru Zhao , Suoshu Zhang , Shifen Li , Lei Jia , Lin Du 1,2,* and Qihua Zhao 1,2,* 1 School of Chemical Science and Technology Pharmacy, Yunnan University, Kunming 650091, China; [email protected] (Y.W.); [email protected] (X.Z.); [email protected] (Y.Z.); [email protected] (S.Z.); [email protected] (S.L.); [email protected] (L.J.) 2 Key Laboratory of Medicinal Chemistry for Natural Resource Education Ministry, Yunnan University, Kunming 650091, China * Correspondence: [email protected] (L.D.); [email protected] (Q.Z.); Tel.: +86-871-6503-5640 (L.D.) These authors contributed equally to this work. y Received: 27 December 2019; Accepted: 12 January 2020; Published: 17 January 2020 Abstract: Three novel Zn-based coordination polymers (CPs), [Zn(MIPA)]n (1), {[Zn(MIPA)(4,40- bipy) (H O)] 1.5H O}n (2), and {[Zn(MIPA)(bpe)] H O}n (3) (MIPA = 4-methoxyisophthalic acid, 0.5 2 · 2 · 2 4,40-bipy = 4,40-bipyridine, bpe = (E)-1,2-di(pyridine-4-yl)ethane), were constructed by ligand 4-methoxyisophthalic acid under solvothermal conditions. Compound 1 features a beaded 2D-layer architecture, while compound 2 presents a 2-fold interpenetrating structure with a uninodal three-connected hcb topology. Compound 3 has a 3-fold interpenetrated four-connected dmp topology. Photoluminescence investigations of compound 2 were explored in detail, by which ions 3+ 2 were detected, and it was observed to have the highest quenching efficiency toward Al and S − ions. 3+ 2 The possible fluorescence quenching mechanisms of 2 toward Al and S − ions were also explored. To the best of our knowledge, this is the first potential dual-responsive luminescent probe based on 3+ 2 a Zn(II) coordination polymer for detecting Al and S − ions via a luminescence quenching effect in ethanol. Keywords: coordination polymers; 4-methoxyisophthalic acid; ion detection; ethanol 1. Introduction As interest in environmental and health concepts grows, the effects of various ions on the biological environment and human health are popular focus points. Aluminum and sulfur ions play an important part in our daily lives and are not able to be substituted due to their peculiarly superior properties, such as the light weight and corrosion resistance of the metal aluminum, and the participation of sulfur ions in physiological processes [1,2]. However, if the aluminum ion or sulfur ion content in the body is high, it will affect human health. The concentration of aluminum ions accumulated in the human body can result in metabolic disorders. Abnormal production of sulfur ions is associated with many diseases, including loss of consciousness and respiratory paralysis [3,4]. In addition, sulfur ions are important pollutants in the environment and are widely found in various polluted water sources. Therefore, it is very important to urgently establish a rapid and effective analytical method for the determination of aluminum and sulfur ions or to find a substance that has a specific and sensitive ability to recognize them. Coordination polymers (CPs) have aroused much interest, owing to their potential applications in catalysis [5–7], adsorption [8,9], separation [10], electrochemistry [11–13], and as chemical Molecules 2020, 25, 382; doi:10.3390/molecules25020382 www.mdpi.com/journal/molecules Molecules 2020, 25, 382 2 of 14 Molecules 2020, 25, x FOR PEER REVIEW 2 of 14 sensors[14–17]. [14In– 17recent]. In years, recent coordination years, coordination polymers polymers (CPs) used (CPs) as used fluorescent as fluorescent sensors sensors have havebeen 3+ 3+ 2− 2 beensuccessfully successfully applied applied in the in determination the determination of various of various analytes analytes such such as metal as metal ions ions (Fe (Fe, Cr2,O Cr4 2,O etc.)4 −, etc.)[18–20], [18– small20], small molecules molecules (acetylacetone, (acetylacetone, water, water, etc.) etc.) [21,22], [21,22 and], and explosives explosives (TNT, (TNT, PA, PA, etc.) etc.) [23–25]. [23–25]. Coordination polymerspolymers have have become become one one of theof the hotspots hotspots of material of material chemistry chemistry as new as fluorescent new fluorescent probes becauseprobes because of their of high their sensitivity high sensitivity and selectivity, and selectivity, ease of operation, ease of operation, convenience, convenience, and fast responseand fast timeresponse [26– 29time]. There[26–29]. has There been evidencehas been thatevidence Zn-based that coordinationZn-based coordination polymers presentpolymers prominent present superiority,prominent superiority, especially inespecially the field in of the fluorescence field of fluo sensingrescence [ 30sensing,31]. He[30,31]. et al. He designed et al. designed a Zn-based a Zn- 3+ 3+3+ 3+ 2 2− 22− multi-responsivebased multi-responsive luminescent luminescent probe prob withe awith discriminatory a discriminatory ability ability for Fe for ,Fe Al, Al, SiF, SiF6 −6, Cr, Cr2O2O77 −,, nitrofurantoin (NFT), and nitrofurazonenitrofurazone (NFZ) viavia thethe changechange ofof luminescenceluminescence intensityintensity [[32].32]. The Zn(II) ion, as aa dd1010 metal ion, can greatly enhance the rigidity and fluorescentfluorescent yield of coordinationcoordination polymers [[33,34].33,34]. Furthermore, Zn-based CPs are able to displaydisplay thethe ligand-centeredligand-centered characteristiccharacteristic emission. AsAs such, such, Zn-based Zn-based CPs CPs used used as fluorescent as fluorescent sensors sensors usually changeusually thechange fluorescence the fluorescence properties byproperties means of by the means incorporation, of the incorporation, functionalization, functionalization, and modification and modification of the ligands of [ 35the,36 ligands]. Therefore, [35,36]. it isTherefore, fascinating it is and fascinating significant and to significant design and to synthesize design and luminescent synthesize materialsluminescent using materials Zn(II) ionsusing and Zn(II) the controlions and of the ligands. control of ligands. Herein, wewe reported reported three three novel Zn-basednovel Zn-based coordination coordination polymers: [Zn(MIPA)] polymers:n (1[Zn(MIPA)]), {[Zn(MIPA)(4,4n (1),0- bipy){[Zn(MIPA)(4,4’-bipy)(H O)] 1.5H O}0.5n (H(2),2O)]·1.5H and {[Zn(MIPA)(bpe)]2O}n (2), andH O}{[Zn(MIPA)(bpe)]·Hn (3) (MIPA = 4-methoxyisophthalic2O}n (3) (MIPA acid, = bpe4- 0.5 2 · 2 · 2 =methoxyisophthalic(E)-1,2-di(pyridine-4-yl)ethane), acid, bpe = which(E)-1,2-di(pyridine-4-yl)ethane), were constructed by introducing which anwere N-donor constructed ligand andby controllingintroducing solvents. an N-donor The solid ligand fluorescence and controlling properties solv of compoundsents. The solid1–3 were fluorescence investigated, properties and results of 3+ 2 clearlycompounds indicated 1–3 thatwere compound investigated,2 has and agood results fluorescence clearly indicated performance that compound in Al and 2 S has− detection, a good withfluorescence high selectivity performance and sensitivity. in Al3+ and As S2 far− detection, as we know, with this high is theselectivity first Zn-based and sensitivity. coordination As far polymer as we 3+ 2 whichknow, canthis be is usedthe first as a dualZn-based functional coordination fluorescent polymer material which to detect can Albe usedand as S −aions dual by functional means of luminescencefluorescent material quenching to detect in ethanol. Al3+ and S2− ions by means of luminescence quenching in ethanol. 2. Results 2.1. Crystal Structure of [Zn(MIPA)]nn (1) Single crystalcrystal X-ray X-ray analysis analysis showed showed that that compound compound1 crystallizes 1 crystallizes in the in orthorhombic the orthorhombic Pbca spacePbca group,space group, presenting presenting a 2D multi-metallic a 2D multi-metallic linear clusterlinear cluster structure. structure. The asymmetrical The asymmetrical unit consists unit consists of one Zn(II)of one ionZn(II) and ion one and MIPA one ligand. MIPA Eachligand. hexacoordinated Each hexacoordinated Zn(II) center Zn(II) with center a ZnO with6 binding a ZnO6 setbinding displays set adisplays distorted a octahedraldistorted octahedral geometry, createdgeometry, by fivecreated carboxylic by five O carboxylic atoms from O fouratoms diff fromerent four MIPA different ligands (Zn–O:MIPA ligands 1.958(4), (Zn–O: 1.997(4), 1.958(4), 2.008(4), 1.997(4), 2.016(4) 2.008(4), Å) and 2. one016(4) methoxy Å) and O one atom methoxy (Zn–O: O 2.482(4) atom (Zn–O: Å) (Figure 2.482(4)1a). 5 TheÅ) (Figure MIPA ligand 1a). The is completely MIPA ligand deprotonated is completely with the deprotonated coordination with mode the of µ coordination4-κ O0,O00,O000 mode,O0000 :Oof00000 μ4-. (Schemeκ5O’,O’’,O1,’’’ mode,O’’’’:O I).’’’’’ Two. (Scheme carboxyl 1, mode groups I). from Two di carboxylfferent MIPA groups ligands fromare different used to MIPA bridge ligands the neighboring are used Zn(II) ions into 1D multi-metallic (Zn–O)n chains (Zn Zn distance is 3.519 Å), and the neighboring to bridge the neighboring Zn(II) ions into 1D multi-metallic··· (Zn–O)n chains (Zn···Zn distance is 3.519 1DÅ), multi-metallicand the neighboring chains are1D furthermulti-metallic connected chains into are a beaded further 2D-layer connected structure into a bybeaded MIPA 2D-layer ligands (Figure1b,c). The 2D-layer structure is further assembled into a 3D supermolecule frame by π π structure by MIPA ligands (Figure 1b,c). The 2D-layer structure is further assembled into a ···3D interactionsupermolecule between frame layers by π··· (Figureπ interaction1d). between layers (Figure 1d). Scheme 1. Coordination modes of an MIPA (4-methoxyisophthalic(4-methoxyisophthalic acid)acid) ligand.ligand. Molecules 2020, 25, 382 3 of 14 Molecules 2020, 25, x FOR PEER REVIEW 3 of 14 Figure 1. (a) Coordination environment of compound 1, [Zn(MIPA)]n.(b) 1D metal chain of 1.
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