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Issue 4, 2014
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Syntheses of quaternary ammonium-containing, trithiocarbonate RAFT agents and hemi-telechelic cationomers

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Abstract

We reported herein a facile and high-yield approach to synthesize a series of trithiocarbonate RAFT agents containing quaternary ammonium functionality in the “R-group”. This new synthetic route first involves the optimized synthesis of 4-(bromomethyl)-N,N,N-trialkyl benzyl ammonium bromide compounds (Br-Ph-NR3, R = Me, Et and Bu), which were subsequently reacted with the alkyl trithiocarbonate anion to directly produce the trithiocarbonate RAFT agent. It was found that the quaternary ammonium group partially degraded when the RAFT agents were used in polymerizations at 120 °C. This issue was overcome by using lower polymerization temperature, which when combined with column chromatography, afforded high purity α-N,N,N-trialkyl benzyl ammonium hemi-telechelic cationomers.

Graphical abstract: Syntheses of quaternary ammonium-containing, trithiocarbonate RAFT agents and hemi-telechelic cationomers

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Submitted
20 Sep 2013
Accepted
29 Oct 2013
First published
07 Nov 2013

Polym. Chem., 2014,5, 1180-1190
Article type
Paper

Syntheses of quaternary ammonium-containing, trithiocarbonate RAFT agents and hemi-telechelic cationomers

L. Zhang, L. R. Cool, C. Wesdemiotis, R. A. Weiss and K. A. Cavicchi, Polym. Chem., 2014, 5, 1180
DOI: 10.1039/C3PY01314F

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