Influence of Helical Structure on Chiral Recognition of Poly(phenylacetylene)s Bearing Phenylcarbamate Residues of L‐Phenylglycinol and Amide Linage as Pendants |
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| Authors: | Chunhong Zhang Rui Ma Hailun Wang Ryosuke Sakai Toshifumi Satoh Toyoji Kakuchi Lijia Liu Yoshio Okamoto |
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| Affiliation: | 1. Polymer Materials Research Center, Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China;2. Department of Materials Chemistry, Asahikawa National College of Technology, Asahikawa, Japan;3. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Chemical Sciences and Engineering, Faculty of Engineering, Hokkaido University, Sapporo, Japan;4. Graduate School of Engineering, Nagoya University, Nagoya, Japan |
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| Abstract: | Four poly(phenylacetylene)s ( PPA-1 , PPA-2 , PPA-3 , PPA-4 ) bearing phenylcarbamate residues of L ‐phenylglycinol and amide linkage as pendants were prepared to be used as chiral stationary phases (CSPs) for high‐performance liquid chromatography (HPLC), and the influences of coating solvents, dimethylformamide (DMF) and tetrahydrofuran (THF), which were used for coating the polymers on silica gel, on the helical structure of the polymers and their chiral recognition abilities were investigated. The structure analysis of PPA-1 , PPA-2 , PPA-3 , PPA-4 by 1H nuclear magnetic resonance (NMR), size exclusion chromatography (SEC), optical rotation, and circular dichroism (CD) spectra indicated that the polymers possess the cis‐transoidal structure with dynamic helical conformation. The polymers in THF seem to have shorter conjugated helical main chains along with a tighter twist conformation than those in DMF. The chiral recognition abilities of PPA-1 , PPA-2 , PPA-3 , PPA-4 with the different helical structures induced by the coating solvents were evaluated as the CSPs in HPLC. The helical structures of PPA-1 , PPA-2 , PPA-3 , PPA-4 induced with THF are preferable for chiral recognition for some racemates compared to those induced with DMF, and higher chiral recognition abilities of PPA-1 , PPA-2 , PPA-3 , PPA-4 were achieved using THF. Chirality 27:500–506, 2015. © 2015 Wiley Periodicals, Inc. |
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| Keywords: | chiral recognition poly(phenylacetylene) helical structure CSP HPLC |
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