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Controllable Synthesis of Stereoregular Polyesters by Organocatalytic Alternating Copolymerizations of Cyclohexene Oxide and Norbornene Anhydrides

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    Controllable Synthesis of Stereoregular Polyesters by Organocatalytic Alternating Copolymerizations of Cyclohexene Oxide and Norbornene Anhydrides
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    † Department of Polymer Science and Engineering, Hebei University of Technology, No. 8 Guangrong Road, Hongqiao District, Tianjin 300130, China
    ‡ The WCU Center for Synthetic Polymer Bioconjugate Hybrid Materials, Department of Polymer Science and Engineering, Pusan National University, Busan 609-735, Korea
    § Institute for Technical and Macromolecular, University of Hamburg, Bundesstrasse 45, D-20146 Hamburg, Germany
    *E-mail [email protected] (B.L.).
    *E-mail [email protected] (I.K.).
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    Cite this: Macromolecules 2015, 48, 11, 3431–3437
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    https://doi.org/10.1021/acs.macromol.5b00555
    Published May 22, 2015
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    Abstract

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    A facile strategy has been demonstrated for the selective synthesis of highly stereoregular polyesters with cis-2,3-(exo, exo) or trans-2,3-(exo, endo) repeating units by the organocatalysts mediated alternating copolymerization of cyclohexene oxide and norbornene anhydride (NA) stereoisomers. The geometrical structure of polyester can be tuned simply by modulating the type of NA isomers (endo- or exo-NA), monomer feed ratio, and reaction temperature. The cis- (>99%) and trans-polyesters (>99%) exhibit high glass transition temperature up to 129.8 and 115.9 °C, respectively. The resulting polyesters provide a versatile platform to incorporate various functional groups through the robust thiol–ene reaction of the pendant norbornenyl groups.

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    Cite this: Macromolecules 2015, 48, 11, 3431–3437
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    https://doi.org/10.1021/acs.macromol.5b00555
    Published May 22, 2015
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