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Synthesis of enantiopure homo and copolymers by raft polymerization and investigation of their enantioselective lipase-catalyzed esterification

Authors

  • Bahar Yeniad,

    1. Laboratory of Polymer Chemistry, Technische Universiteit Eindhoven, Den Dolech 2, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    2. Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands
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  • N. Oruç Köklükaya,

    1. Laboratory of Polymer Chemistry, Technische Universiteit Eindhoven, Den Dolech 2, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
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  • Hemantkumar Naik,

    1. Laboratory of Polymer Chemistry, Technische Universiteit Eindhoven, Den Dolech 2, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
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  • M. W. Martin Fijten,

    1. Laboratory of Polymer Chemistry, Technische Universiteit Eindhoven, Den Dolech 2, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
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  • Cor E. Koning,

    1. Laboratory of Polymer Chemistry, Technische Universiteit Eindhoven, Den Dolech 2, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    2. Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands
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  • Andreas Heise

    Corresponding author
    1. Laboratory of Polymer Chemistry, Technische Universiteit Eindhoven, Den Dolech 2, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
    2. School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland
    • Laboratory of Polymer Chemistry, Technische Universiteit Eindhoven, Den Dolech 2, P.O. Box 513, 5600 MB Eindhoven, The Netherlands
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Abstract

Homo and copolymers were synthesized from enantionpure (R)- and (S)-1-(4-vinylphenyl)ethanol by reversible addition-fragmentation chain transfer polymerization. The polymerization conditions were optimized resulting in dioxane as the preferred reaction solvent. First-order polymerization kinetics and well-defined enantiopure homopolymers with low dispersities were obtained. In agreement with their enantiomeric composition, the (R) and (S)-polymers gave opposite optical rotation of light. Polymer analogous esterification of the chiral hydroxy groups catalyzed by enantioselective Candida antarctica Lipase B was strongly (R)-selective. Esterification on the homopolymer and copolymers could be achieved to a maximum of around 50 %. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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