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Side-Chain Modification and “Grafting Onto” via Olefin Cross-Metathesis

Authors

  • Lucas Montero de Espinosa,

    1. Laboratory of Applied Chemistry, Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
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  • Kristian Kempe,

    1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Philosophenweg 7, 07743 Jena, Germany
    2. Jena Center of Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany
    Current affiliation:
    1. Nanostructured Interfaces and Materials group, Department of Chemical & Biomolecular Engineering, The University of Melbourne, Parkville, Victoria 3010, Australia
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  • Ulrich S. Schubert,

    1. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich-Schiller-University Jena, Philosophenweg 7, 07743 Jena, Germany
    2. Jena Center of Soft Matter (JCSM), Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany
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  • Richard Hoogenboom,

    Corresponding author
    1. Supramolecular Chemistry Group, Department of Organic Chemistry, Ghent University, Krijgslaan 281 S4, 9000 Ghent, Belgium
    • Supramolecular Chemistry Group, Department of Organic Chemistry, Ghent University, Krijgslaan 281 S4, 9000 Ghent, Belgium.
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  • Michael A. R. Meier

    Corresponding author
    1. Laboratory of Applied Chemistry, Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
    • Laboratory of Applied Chemistry, Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
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Abstract

Olefin cross-metathesis is introduced as a versatile polymer side-chain modification technique. The reaction of a poly(2-oxazoline) featuring terminal double bonds in the side chains with a variety of functional acrylates has been successfully performed in the presence of Hoveyda–Grubbs second-generation catalyst. Self-metathesis, which would lead to polymer–polymer coupling, can be avoided by using an excess of the cross-metathesis partner and a catalyst loading of 5 mol%. The results suggest that bulky acrylates reduce chain–chain coupling due to self-metathesis. Moreover, different functional groups such as alkyl chains, hydroxyl, and allyl acetate groups, as well as an oligomeric poly(ethylene glycol) and a perfluorinated alkyl chain have been grafted with quantitative conversions.

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