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Efficient click-addition sequence for polymer–polymer couplings

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Brendel, Johannes C., Gody, Guillaume and Perrier, Sébastien (2016) Efficient click-addition sequence for polymer–polymer couplings. Polymer Chemistry, 7 (35). pp. 5536-5543. doi:10.1039/C6PY00954A

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Official URL: http://dx.doi.org/10.1039/C6PY00954A

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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
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Polymerization, Polymers, Block copolymers
Journal or Publication Title: Polymer Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1759-9954
Official Date: 9 August 2016
Dates:
DateEvent
9 August 2016Available
5 August 2016Accepted
2 June 2016Submitted
Volume: 7
Number: 35
Page Range: pp. 5536-5543
DOI: 10.1039/C6PY00954A
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
Funder: Royal Society (Great Britain). Wolfson Research Merit Award (RSWRMA), Monash-Warwick Alliance, Deutsche Forschungsgemeinschaft (DFG)
Grant number: WM130055 (RSWRMA), BR4905/1 - 1 (DFG)

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