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-Francois (2011) Orthogonal modification of polymer chain-ends via sequential nitrile oxide-alkyne and azide-alkyne Huisgen cycloadditions. Polymer Chemistry, 2 (2). pp. 372-375. ISSN 1759-9954

Full content URL: http://dx.doi.org/10.1039/c0py00236d

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Item Type:Article
Item Status:Live Archive

Abstract

The alpha- and omega-chain-ends of well-defined polystyrene chains were functionalized using consecutive Huisgen cycloadditions. Firstly, an alpha-alkyne, omega-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.

Additional Information:First published online 04 Oct 2010
Keywords:Chemistry
Subjects:B Subjects allied to Medicine > B200 Pharmacology, Toxicology and Pharmacy
Divisions:College of Science > School of Pharmacy
ID Code:11296
Deposited On:25 Jul 2013 15:03

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