Syntheses of Novel Chiral Polymethacrylates Using Unsaturated Isocyanate and Chiral Recognition Ability

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  • OISHI Tsutomu
    Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University
  • LEE Yong-kyung
    Yamaguchi TLO
  • ONIMURA Kenjiro
    Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Yamaguchi University

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Other Title
  • 不飽和イソシアナートを用いた新規キラルポリメタクリレートの合成と不斉認識能
  • フホウワ イソシアナート オ モチイタ シンキ キラル ポリメタクリレート ノ ゴウセイ ト フセイ ニンシキノウ

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Description

Chiral methacrylates (RMOC, RMOU) having an urethane or urea bond were synthesized from the reaction of 2-methacryloyloxyethyl isocyanate (MOI) and optically active alcohols or amines, such as cholesterol, L-menthol, amino acid derivatives, cinchonine, (S) methylbenzylamine, (R) -1- (1-naphthyl) ethylamine, and so on. Radical polymerizations of RMOC and RMOU were carried out using azobisisobutyronitrile (AIBN) to obtain corresponding optically active polymers having hydrogen bonds caused by urethane or urea segments. Chiroptical properties of poly (RMOC) and poly (RMOU) were affected by temperature. This may be attributed to change of conformation caused by hydrogen bonds and/or interaction between substituents in the side chain. From the results of radical copolymerizations of RMOC or RMOU with styrene (ST), methyl methacrylate (MMA), or butyl methacrylate (BMA), monomer reactivity ratios (r1, r2) and Alfrey-Price Q-e were determined. Chiroptical properties of the copolymers were strongly influenced by comonomer units. To examine chiral recognition abilities of poly (RMOC) and poly (RMOU), chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were prepared from silica gel, poly (RMOC), and poly (RMOU). The CSPs resolved racemates 1 to 16, and the chiral recognition abilities of poly (RMOC) and poly (RMOU) may be ascribed to the secondary and/or higher-ordered structure of the polymers.

Journal

  • KOBUNSHI RONBUNSHU

    KOBUNSHI RONBUNSHU 61 (4), 216-226, 2004

    The Society of Polymer Science, Japan

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