Synthesis of poly(phenylacetylene)s containing chiral phenylethyl carbamate residues as coated-type CSPs with high solvent tolerability |
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| Authors: | Yanli Zhou Ruiqi Zhu Chunhong Zhang Xudong Liu Zhongpeng Wang Zhengjin Zhou Lijia Liu Hongxing Dong Toshifumi Satoh Yoshio Okamoto |
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| Institution: | 1. Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China;2. Faculty of Engineering, Hokkaido University, Sapporo, Japan;3. Key Laboratory of Superlight Materials and Surface Technology, Ministry of Education, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin, China
Graduate School of Engineering, Nagoya University, Nagoya, Japan |
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| Abstract: | Two novel helical poly(phenylacetylene) derivatives containing chiral phenylethyl carbamate residues in the end of each side chain ( PPA-S and PPA-R ) were synthesized by polymerization of the corresponding phenylacetylene monomers using Rh(nbd)BPh4 as a catalyst in DMF. The enantioseparation properties of the polymers were evaluated as coated-type chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). Under the same chromatographic conditions, PPA-S and PPA-R showed different enantioseparation properties, indicating that the different interactions between the analytes and the polymers, which result from the different chiral phenylethyl carbamate groups in the end of each side chains. Racemates 1 , 7 , and 8 could be better resolved on PPA-S , while racemate 6 was separated on PPA-R more efficiently. In addition, the coated-type CSPs showed good solvent tolerability and could work without any damage by introducing the polar solvents, such as CHCl3 and THF, in eluent. Moreover, some racemates could be better resolved on these coated-type CSPs with the addition of THF to the eluent. |
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| Keywords: | chiral phenylethyl carbamate CSP enantioseparation helical poly(phenylacetylene) HPLC solvent tolerability |
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