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Two-Step Template Method for Synthesis of Axis-Length- Controlled Porphyrin-Containing Hollow Structures

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Two-Step Template Method for Synthesis of Axis-Length- Controlled Porphyrin-Containing Hollow Structures ChemComm Two-Step Template Method for Synthesis of Axis-Length- Controlled Porphyrin-Containing Hollow Structures Journal: ChemComm Manuscript ID CC-COM-04-2019-002866.R2 Article Type: Communication Page 1 of 4 Please doChemComm not adjust margins COMMUNICATION Two-Step Template Method for Synthesis of Axis-Length- Controlled Porphyrin-Containing Hollow Structures a,b c c a a a Received 00th January 20xx, Yusuke Chiba, Yuki Oka, Hiroshi Masai, Wakana Matsuda, Tetsuaki Fujihara, Yasushi Tsuji, Accepted 00th January 20xx and Jun Terao*c,d DOI: 10.1039/x0xx00000x π− Conjugated porphyrin-containing hollow structures with defined Previous Work (ref 9) This Work axis-length were successfully synthesized by a two-step template method, i.e., template-assisted cyclization and oligomerization. During the oligomerization, templates played important roles in controlling the reaction rates and the axis lengths. The hollow ⅰ) ⅱ) Branched polymer structures exhibited an extended effective π−conjugation because ⅰ) of the high coplanarity between porphyrins. b Top view a d Coordination points a θ b d c c θ = 0.3° Te m p la te ⅲ Host molecules with one dimentional (1D) hollow structures ⅲ) (m ultidantate) ⅲ) am ine ligand) n have attracted attention for use in channels and achievement of unique molecular arrangement in host–guest chemistry because of their one-dimensional cavity.1 The functions of the host–guest complexes can be manipulated by the molecular n ⅳ) structures and components. In particular, porphyrin-containing ⅳ) ⅳ) hollow structures are expected to provide 1D functional cavities, because porphyrins show unique optical properties and catalytic abilities.2 For example, molecular tubes consisting n of porphyrins (porphyrin tubes) can align fullerenes3 in one n = 0 or 1 π dimension using the planes of porphyrins; this characteristic Figure 1. Template synthesis of porphyrin-containing hollow is exhibited by photovoltaic materials.4 Such functions of the structures (left: previous method, right: this method); (i) porphyrin-containing hollow structures depend on the cavity dimerization, (ii) template-assisted cyclization, (iii) complexation, sizes and axis lengths. To realize defined functions of the hollow and (iv) template-assisted oligomerization. θ means the structures, it is necessary to develop synthetic methods for structure-controlled porphyrin-containing hollow structures. angle between directions ab (red line) and cd (blue line), and DFT Previous porphyrin-containing hollow structures were constructed calculations showed that the angle of the porphyrin ring is 0.3° by one-dimensional alignment of ring structures composed of (Figure S12, ESI†). multiple porphyrins, named porphyrin rings. The binding modes among the porphyrin rings are categorized into two types. One is a. Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, non-covalent bonding: Aida and Tani successfully constructed Japan b. Present address: Graduate School of Pure and Applied Sciences and Tsukuba porphyrin tubes by intermolecular hydrogen bonds and π–π Research Center for Energy Materials Science (TREMS), University of Tsukuba, 1- interactions among the porphyrin rings, providing hollow 1-1 Tennodai,Tsukuba, Ibaraki 305-8571 4,5 c. Graduate School of Arts and Sciences, The University of Tokyo, Meguro-ku, Tokyo structures. The other binding mode is covalent bonding. Covalently 153-8902, Japan linked porphyrins show efficient charge transport6a and non-linear d. School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, 6b Japan optical properties due to the π electron delocalization among E-mail: [email protected] porphyrins. Therefore, porphyrin-containing hollow structures in † Electronic Supplementary Information (ESI) available. See DOI: 10.1039/x0xx00000x which porphyrin rings are linked by covalent bonding are promising Please do not adjust margins Please doChemComm not adjust margins Page 2 of 4 COMMUNICATION Journal Name for a unit of electronic/optical materials and host molecules that directions ab and cd (Figure 1, right center) are horizontally aligned align guest molecules. However, to construct the 1D cavity with to increase the proximity of the reaction points. To realize the porphyrin rings needs the formations of the multiple covalent alignment, it is important to design a strain-free porphyrin ring. A bondings between the porphyrin rings. These ladder polymerization previous porphyrin ring, which comprised of nickel porphyrins and is required to suppress the production of byproducts, including m-phenylenes was designed, and the angle, θ, between directions ab branched polymers (Figure 1, upper right). and cd was determined to be 25.2° in the crystal structure.4b The Template methods that employ coordination bonding between zinc torsion is assumed to arise from the saddle-shaped porphyrins and porphyrins and amines have been used to prepare challenging curved diynes. In this study, we designed a square porphyrin dimer, structures, such as length-defined porphyrin oligomers7 and cavity ZnCP’, comprised of planar zinc porphyrin and rectangular fluorene size-defined porphyrin rings.8 Chujo, Hupp, and Anderson reported units (Scheme 1). DFT calculations showed that the optimized the template-assisted synthesis of porphyrin-containing hollow structure had a torsion-less square structure; the angle, θ, was 0.3° structures from linear porphyrin dimers (trimers) via sequential (Figure S12, ESI†). Generally, extended π−conjugated molecules have dimerization (trimerization), complexation, and template-assisted low solubilities in organic solvents due to weak intermolecular cyclic oligomerization (Figure 1, left).9 In the template synthesis, the interactions, such as π–π and CH–π.10 To increase the solubility, eight numbers of coordination points in the templates and shapes, control esters were introduced to the fluorene units, outside of the square the cavity sizes of the hollow structures. Furthermore, Anderson porphyrin dimer. reported a synthetic method for porphyrin tubes via cyclization, π- Recently, we reported the selective synthesis of a square elongation, and cyclic oligomerization.9d However, these methods porphyrin dimer derivative, ZnCP’ (Scheme 1), via template- require precursors with predefined lengths. A template method for assisted cyclization (Figure 1, right ii).11 In this study, we the selective synthesis of porphyrin-containing hollow structures investigated the complexation abilities of ZnCP’ and the with defined-axis length from a single porphyrin ring is required. templates (Figure 1, right iii). We designed templates, T2 (n = 4, We envisage that the oligomerization of cyclic porphyrins using 6, 8, and 12), with two 1,4-di(pyridin-4-yl)benzene units linked templates has the potential to be applied in preparing by alkyl chains for dimerization (Figure 2). Different lengths of structure-controlled porphyrin-containing hollow structures alkyl chains were introduced to the templates to evaluate the with high efficiency. The method comprises two stepwise effect of the length on the oligomerization. T2’ (n = 6) is template-assisted processes: template-assisted cyclization employed as a reference molecule to T2 (n = 6) in investigating complexation, and template-assisted oligomerization (Figure 1, the relationship between the association constant and the right). The axis lengths of the hollow structures can be reaction. The ratio of ZnCPs to the templates T2 (n = 4, 8, and controlled by the numbers of coordination points and shapes of 12) in the complexes was 2:1, as confirmed by 1H NMR titration the templates. We anticipated that oligomerization would occur experiments in CDCl3 (Figures S1-S5, ESI†). These results among porphyrin rings on the templates to prohibit excess confirmed that the proximity of the two ZnCPs increased via the reactions under a high dilution condition. Herein, we describe a complexation. two-step template method to prepare structure-controlled As the template-assisted oligomerization, we selected the porphyrin-containing hollow structures. Glaser reaction. The transition state of the Glaser reaction goes The molecular design is described below. A key prerequisite for the through horizontal arrays of two copper acetylides; therefore, oligomerization of the precursor is that two opposite porphyrins in the reaction is expected to be suitable for the synthesis of porphyrin-containing hollow structures with coplanar and 12 Scheme 1. Complexation between ZnCP’ and T2 (n = x). linear porphyrins. In fact, the Glaser reaction incorporating a R R copper catalyst is known to be effective for molecules with Ph R N Ph R N Zn N 13 R R N N Ph N high linearity. In this study, we prepared a Zn-square R Zn R N N N Ph N R Ph N Zn N R porphyrin dimer, ZnCP, with alkynes on porphyrins (see ESI†). Ph N N R O Template-assisted synthesis of was carried out by R ZnCP2 T2 (n = x) O R oligomerization of ZnCP. The Glaser reaction of ZnCP with T2 (n CDCl3 R N -6 N Ph = 6) under a highly diluted condition (7.6 × 10 M) selectively Ph R N Zn N R N Ph N R N N R afforded ZnCP2, whereas the reaction hardly proceeded in the N ZnN N Ph R R N Zn N R Ph Ph N R absence of T2 (n = 6) (Figures 3a and 3b). The templates were ZnCP' R R removed by filtration using silica gel (CH2Cl2/EtOAc/pyridine = 100/10/1, v/v/v). Subsequently, ZnCP2 was isolated in 25% N N N N N yield by size exclusion chromatography (toluene/pyridine = O O O O O O 100/1, v/v) of the obtained mixture. ZnCP2 was characterized
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