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Issue 2, 2011
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Orthogonal modification of polymer chain-ends via sequential nitrile oxidealkyne and azidealkyne Huisgen cycloadditions

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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 oxidealkyne cycloaddition (NOAC) and copper-catalyzed azidealkyne 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.

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

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Publication details

The article was received on 29 Jul 2010, accepted on 10 Sep 2010 and first published on 04 Oct 2010


Article type: Paper
DOI: 10.1039/C0PY00236D
Citation: Polym. Chem., 2011,2, 372-375
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    Orthogonal modification of polymer chain-ends via sequential nitrile oxidealkyne and azidealkyne Huisgen cycloadditions

    I. Singh, Z. Zarafshani, F. Heaney and J. Lutz, Polym. Chem., 2011, 2, 372
    DOI: 10.1039/C0PY00236D

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