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

Longhe Zhang; Lydia R. Cool; Chrys Wesdemiotis; R. A. Weiss; Kevin A. Cavicchi

doi:10.1039/C3PY01314F

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

Longhe Zhang,^a Lydia R. Cool,^b Chrys Wesdemiotis,^b R. A. Weiss^a and Kevin A. Cavicchi*^a

* Corresponding authors

^a Department of Polymer Engineering, The University of Akron, Akron, USA
E-mail: kac58@uakron.edu
Fax: +1 330 972 3406
Tel: +1 330 972 8368

^b Department of Chemistry, The University of Akron, Akron, USA

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.

Supplementary files

Article type: Paper

DOI: 10.1039/C3PY01314F

Citation: Polym. Chem., 2014,5, 1180-1190

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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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Polymer Chemistry

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

Abstract

Supplementary files

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

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