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Issue 2, 2016

Dithiocarbamate RAFT agents with broad applicability – the 3,5-dimethyl-1H-pyrazole-1-carbodithioates

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Abstract

3,5-Dimethyl-1H-pyrazole-1-carbodithioates are shown to be extremely versatile dithiocarbamate RAFT agents with wide-spread applicability. The cyanomethyl and benzyl dithiocarbamates offer very low dispersities (Đ < 1.1) for polymers based on more activated monomers [MAMs: methyl acrylate (MA), N,N-dimethylacrylamide (DMA) and styrene (St)] and Đ < 1.3 in polymerization of vinyl acetate (VAc), a less activated monomer (LAM). The tertiary, 2-cyano-2-butyl dithiocarbamate, provides molar mass control and Đ < 1.5 in methyl methacrylate (MMA) polymerization. Lower dispersities can be obtained for MMA copolymers. End group fidelity was proved with the synthesis of block copolymers, poly(DMA)-block-poly(MA). With the ability to control polymerization of both MAMs and LAMs, the RAFT agents were also shown to be suitable for the synthesis of a poly(MAM)-block-poly(LAM), specifically poly(DMA)-block-poly(VAc). The RAFT agents are an appropriate replacement for trithiocarbonate RAFT agents in most circumstances and have the distinct advantage that the RAFT agents have low odour and the derived polymers do not develop odour on storage (i.e., no low molar mass thiols are generated).

Graphical abstract: Dithiocarbamate RAFT agents with broad applicability – the 3,5-dimethyl-1H-pyrazole-1-carbodithioates

Supplementary files

Article information


Submitted
29 Aug 2015
Accepted
04 Nov 2015
First published
06 Nov 2015

Polym. Chem., 2016,7, 481-492
Article type
Paper
Author version available

Dithiocarbamate RAFT agents with broad applicability – the 3,5-dimethyl-1H-pyrazole-1-carbodithioates

J. Gardiner, I. Martinez-Botella, J. Tsanaktsidis and G. Moad, Polym. Chem., 2016, 7, 481 DOI: 10.1039/C5PY01382H

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