Isahak, Naatasha, Gody, Guillaume, Malins, Lara R., Mitchell, Nicholas J., Payne, Richard J. and Perrier, Sébastien (2016) Single addition of an allylamine monomer enables access to end-functionalized RAFT polymers for native chemical ligation. Chemical Communications, 52 (88). pp. 12952-12955. doi:10.1039/C6CC06010B ISSN 1359-7345.

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Abstract

Controlled radical polymerization methods and click chemistry form a versatile toolbox for creating complex polymer architectures. However, the incompatibility between the functional groups required for click reactions and the reaction conditions of radical polymerization techniques often limits application. Here, we demonstrate how combining two complementary click reactions in a sequence circumvents compatibility issues. We employ isocyanate-amine addition on a polymer obtained by RAFT without purification, thus allowing us to work at exact equimolarity. The addition of commercially available amine-functional azido or strained alkyne compounds, yields orthogonally modified polymers, which can be coupled together in a subsequent strain promoted cycloaddition (SPAAC). The efficiency of this reaction sequence is demonstrated with different acrylate, methacrylate, and acrylamide polymers giving block copolymers in high yield. The resulting diblock copolymers remain active towards RAFT polymerization, thus allowing access to multiblock structures by simple chain extension. The orthogonality of the isocyanate-amine reaction, SPAAC and RAFT polymerization (both in terms of monomer and chain end groups) is a key advantage and offers access to functional and challenging polymer architectures without the need for stringent reaction conditions or laborious intermediate purifications.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry T Technology > TP Chemical technology
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH):	Addition polymerization, Polymers, Monomers, Peptides, Fragmentation reactions
Journal or Publication Title:	Chemical Communications
Publisher:	Royal Society of Chemistry
ISSN:	1359-7345
Official Date:	23 September 2016
Dates:	Date Event 23 September 2016 Available 21 September 2016 Accepted 21 July 2016 Submitted
Volume:	52
Number:	88
Page Range:	pp. 12952-12955
DOI:	10.1039/C6CC06010B
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Date of first compliant deposit:	14 November 2016
Date of first compliant Open Access:	23 September 2017
Funder:	Australia. Department of Education, Science, and Training, Australian Research Council (ARC), Royal Society (Great Britain). Wolfson Research Merit Award (RSWRMA), Monash-Warwick Alliance
Grant number:	T130100150 (ARC), WM130055 (RSWRMA)

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