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Influence of stereoregularity and linkage groups on chiral recognition of poly(phenylacetylene) derivatives bearing L-leucine ethyl ester pendants as chiral stationary phases for HPLC

Authors

  • Chunhong Zhang,

    Corresponding author
    1. Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China
    2. Key Laboratory of Superlight Materials and Surface Technology, College of Materials Science and Chemical Engineering, Harbin Engineering University, Ministry of Education, Harbin 150001, China
    • Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China

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  • Fangbin Liu,

    1. Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China
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  • Yufa Li,

    1. Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China
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  • Xiande Shen,

    1. Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China
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  • Xiaodong Xu,

    1. Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China
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  • Ryosuke Sakai,

    1. Department of Materials Chemistry, Asahikawa National College of Technology, Asahikawa 071-8142, Japan
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  • Toshifumi Satoh,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
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  • Toyoji Kakuchi,

    1. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
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  • Yoshio Okamoto

    Corresponding author
    1. Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China
    2. Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan
    • Polymer Materials Research Center, College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China

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Abstract

Stereoregular poly(phenylacetylene) derivatives bearing L-leucine ethyl ester pendants, poly-1 and poly-2a, were, respectively, synthesized by the polymerization of N-(4-ethynylphenylcarbamoyl)-L-leucine ethyl ester (1) and N-(4-ethynylphenyl-carbonyl)-L-leucine ethyl ester (2) using Rh(nbd)BPh4 as a catalyst, while stereoirregular poly-2b was synthesized by solid-state thermal polymerization of 2. Their chiral recognition abilities for nine racemates were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) after coating them on silica gel. Both poly-1 and poly-2a with a helical conformation showed their characteristic recognition depending on coating solvents and the linkage groups between poly(phenylacetylene) and L-leucine ethyl ester pendants. Poly-2a with a shorter amide linkage showed higher chiral recognition than poly-1 with a longer urea linkage. Coating solvents played an important role in the chiral recognition of both poly-1 and poly-2a due to the different conformation of the polymer main chains induced by the solvents. A few racemates were effectively resolved on the poly-2a coated with a MeOH/CHCl3 (3/7, v/v) mixture. The separation factors for these racemates were comparable to those obtained on the very popular CSPs derived from polysaccharide phenylcarbamates. Stereoirregular poly-2b exhibited much lower chiral recognition than the corresponding stereoregular, helical poly-2a, suggesting that the regular structure of poly(phenylacetylene) main chains is essential to attain high chiral recognition. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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