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:	Publisher
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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