Issue 2, 2011
From the journal:

Polymer Chemistry

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

Ishwar Singh,a   Zoya Zarafshani,b   Frances Heaney*a  and  Jean-François Lutz*b  

* Corresponding authors

a Department of Chemistry, National University of Ireland, Maynooth, Co. Kildare, Republic of Ireland
E-mail: mary.f.heaney@nuim.ie
Fax: +353 1 708 3815
Tel: +353 1 708 3802

b Fraunhofer Institute for Applied Polymer Research, Geiselbergstrasse 69, Potsdam, Germany
E-mail: lutz@iap.fhg.de
Fax: +49 331 568 3000
Tel: +49 331 568 1127

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.

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

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Article information

DOI
https://doi.org/10.1039/C0PY00236D
Article type
Paper
Submitted
29 Jul 2010
Accepted
10 Sep 2010
First published
04 Oct 2010

Polym. Chem., 2011,2, 372-375

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

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

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