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    Orthogonal modification of polymer chain-ends via sequential nitrile oxide–alkyne and azide–alkyne Huisgen cycloadditions


    Singh, Ishwar and Zarafshani, Zoya and Heaney, Frances and Lutz, Jean-François (2011) Orthogonal modification of polymer chain-ends via sequential nitrile oxide–alkyne and azide–alkyne Huisgen cycloadditions. Ploymer Chemistry, 2. pp. 372-375. ISSN 1759-9954

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    Abstract

    The α- and ω-chain-ends of well-defined polystyrene chains were functionalized using consecutive Huisgen cycloadditions. Firstly, an α-alkyne, ω-azido heterotelechelic polystyrene precursor was synthesized in three steps: (i) atom transfer radical polymerization in the presence of (1,1,1-trimethylsilyl)-2-propynyl 2-bromo-2-isobutyrate, (ii) deprotection of the alkyne function of the initiator and (iii) nucleophilic substitution of the bromine chain-end of the polymer with sodium azide. Afterwards, the chain-ends of the polymer were modified by successive nitrile oxide–alkyne cycloaddition (NOAC) and copper-catalyzed azide–alkyne cycloaddition (CuAAC). 2 Model building blocks were tested for NOAC, while 4 building blocks were studied for CuAAC. In all cases, the orthogonal combination of NOAC and CuAAC allowed the preparation of tailored heterotelechelic polymers.

    Item Type: Article
    Keywords: Orthogonal modification of polymer chain-ends; sequential nitrile oxide–alkyne; azide–alkyne Huisgen cycloadditions;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 4296
    Depositing User: Dr. Frances Heaney
    Date Deposited: 09 Apr 2013 13:38
    Journal or Publication Title: Ploymer Chemistry
    Publisher: Royal Society of Chemistry
    Refereed: Yes
    URI:

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