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Ring-Opening Metathesis Polymerization of Amino Acid-Functionalized Norbornene Diamide Monomers: Polymerization Behavior and Chiral Recognition Ability of the Polymers

Authors

  • Sutthira Sutthasupa,

    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615-8510, Japan
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  • Fumio Sanda,

    Corresponding author
    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615-8510, Japan
    • Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615-8510, Japan.
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  • Toshio Masuda

    Corresponding author
    1. Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615-8510, Japan
    • Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615-8510, Japan.
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Abstract

Amino acid-derived novel norbornene monomers were synthesized and polymerized with ruthenium catalysts. The polymerization rates were affected by the stereo structure of the monomers; exo,exo-NBL underwent ROMP faster to give the polymers in higher yields than the endo,exo-counterpart. The Grubbs 2nd generation catalyst was the most effective for the amino acid-based monomers. A polymer gel was synthesized by the copolymerization of exo,exo-NBL with 2.5 mol-% of bifunctional norbornene monomer. The gel adsorbed larger amounts of (R)-phenylalaninol and N-(benzyloxycarbonyl)alanine than those of the (S)-isomers.

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