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Issue 7, 2012
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Modular oxime functionalization of well-defined alkoxyamine-containing polymers

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Abstract

Phthalamide-protected O-(4-vinylbenzyl)-hydroxylamine was polymerized via reversible addition-fragmentation chain transfer (RAFT) polymerization with good control of the polymer molecular weight and retention of chain end functionality. The resulting polymer was deprotected by cleavage of the phthalamido protecting groups via treatment with hydrazine to reveal the latent side-chain alkoxyamine functionality (R–O–NH2). The alkoxyamine polymer scaffold was coupled with model small molecule aldehydes and ketones via highly efficient “click” oxime bond formation. The ability of the coupling reactions to be conducted at a variety of temperatures, in the presence of oxygen, and without any additional reagents makes this an attractive modular strategy for preparing well-defined polymers with high degrees of functionality.

Graphical abstract: Modular oxime functionalization of well-defined alkoxyamine-containing polymers

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Article information


Submitted
30 Sep 2011
Accepted
24 Oct 2011
First published
07 Nov 2011

Polym. Chem., 2012,3, 1758-1762
Article type
Paper

Modular oxime functionalization of well-defined alkoxyamine-containing polymers

M. R. Hill, S. Mukherjee, P. J. Costanzo and B. S. Sumerlin, Polym. Chem., 2012, 3, 1758
DOI: 10.1039/C1PY00451D

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