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Precision PEGylated Polymers Obtained by Sequence-Controlled Copolymerization and Postpolymerization Modification

Authors

  • Sansanee Srichan,

    1. Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034 Strasbourg Cedex 2 (France)
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  • Dr. Hatice Mutlu,

    1. Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034 Strasbourg Cedex 2 (France)
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  • Dr. Nezha Badi,

    1. Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034 Strasbourg Cedex 2 (France)
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  • Dr. Jean-François Lutz

    Corresponding author
    1. Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034 Strasbourg Cedex 2 (France)
    • Precision Macromolecular Chemistry Group, Institut Charles Sadron, CNRS-UPR 22, 23 rue du Loess, 67034 Strasbourg Cedex 2 (France)

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  • Funding for the research leading to these results was received from the European Research Council under the European Union Seventh Framework Program (FP7/2007-2013)/ERC grant agreement no. 258593. The CNRS, the University of Strasbourg, the International Center for Frontier Research in Chemistry (icFRC), and the excellence network Chemistry of Complex Systems (LabEx CSC) are also acknowledged for financial support. We thank Marc Karman, Clément Lepori, and Laurence Oswald (Institut Charles Sadron, Strasbourg) for the synthesis and NMP of PEG macromonomers, as well as Catherine Foussat and Mélanie Legros (Institut Charles Sadron, Strasbourg) for the SEC measurements.

Abstract

Copolymers containing water-soluble poly(ethylene glycol) (PEG) side chains and precisely controlled functional microstructures were synthesized by sequence-controlled copolymerization of donor and acceptor comonomers, that is, styrene derivatives and N-substituted maleimides. Two routes were compared for the preparation of these structures: a) the direct use of a PEG–styrene macromonomer as a donor comonomer, and b) the use of an alkyne-functionalized styrenic comonomer, which was PEGylated by copper-catalyzed alkyne–azide cycloaddition after polymerization. The latter method was found to be the most versatile and enabled the synthesis of high-precision copolymers. For example, PEGylated copolymers containing precisely positioned fluorescent (e.g. pyrene), switchable (e.g. azobenzene), and reactive functionalities (e.g. an activated ester) were prepared.

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