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Issue 19, 2014

Fast conversion of terminal thiocarbonylthio groups of RAFT polymers to “clickable” thiol groups via versatile sodium azide

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Abstract

This work reports a facile and fast way of removing thiocarbonylthio end groups of RAFT-made polymers by the utilization of sodium azide (NaN3) without deoxygenation. Within several minutes (1–5 minutes), the terminal thiocarbonylthio group of RAFT-made polybutylacrylate (PBA) was completely removed upon NaN3 treatment as revealed by nuclear magnetic resonance. Careful identification of the chain end structure of the resultant polymer was implemented by matrix-assisted laser desorption ionization time-of-flight mass spectrometry, and the results unambiguously proved that the terminal thiocarbonylthio group was converted to the “clickable” thiol group by NaN3via a nucleophilic process. Polystyrene, poly(methyl methacrylate) and poly(vinyl acetate) prepared by the RAFT technique with different kinds of RAFT agents have also been examined under identical conditions. Similar results were obtained, demonstrating a good universality of this approach. This work provides an alternative and effective approach for removing/modifying thiocarbonylthio end groups of RAFT-made polymers, while producing “clickable” thiol-terminated polymers for many post-modification possibilities.

Graphical abstract: Fast conversion of terminal thiocarbonylthio groups of RAFT polymers to “clickable” thiol groups via versatile sodium azide

Supplementary files

Article information


Submitted
25 May 2014
Accepted
17 Jun 2014
First published
17 Jun 2014

Polym. Chem., 2014,5, 5546-5550
Article type
Communication
Author version available

Fast conversion of terminal thiocarbonylthio groups of RAFT polymers to “clickable” thiol groups via versatile sodium azide

Y. Wu, Y. Zhou, J. Zhu, W. Zhang, X. Pan, Z. Zhang and X. Zhu, Polym. Chem., 2014, 5, 5546 DOI: 10.1039/C4PY00732H

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