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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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Publication details

The article was received on 30 Sep 2011, accepted on 24 Oct 2011 and first published on 07 Nov 2011


Article type: Paper
DOI: 10.1039/C1PY00451D
Polym. Chem., 2012,3, 1758-1762

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    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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