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Issue 12, 2014
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Multiblock sequence-controlled glycopolymers via Cu(0)-LRP following efficient thiol–halogen, thiol–epoxy and CuAAC reactions

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Abstract

The combination of copper(0) mediated living radical polymerization (Cu(0)-LRP) with thiol–halogen, thiol–epoxy and copper catalysed alkyne azide coupling (CuAAC) click chemistry has been employed to give a new route to multiblock sequence-controlled glycopolymers. Multiblock poly(glycidyl acrylate)-co-(acrylic acid 3-trimethylsilanyl-prop-2-ynyl ester) (poly(GA)-co-(TMSPA)) were obtained by Cu(0)-LRP in DMSO at ambient temperature via iterative monomer addition whereby the sequence of the multi blocks is attained in a designed way. Thiol–halogen and thiol–epoxy reaction of poly(GA) have been exploited, which suggested a preference for the reaction of the halogen rather than the epoxide for the thiol with triethyl amine as catalyst. The obtained multiblock poly(GA)-co-(TMSPA) were then used for sequential thiol–halogen, thiol–epoxy and CuAAC reactions to build functional glycopolymers in defined sequence.

Graphical abstract: Multiblock sequence-controlled glycopolymers via Cu(0)-LRP following efficient thiol–halogen, thiol–epoxy and CuAAC reactions

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Supplementary files

Article information


Submitted
05 Mar 2014
Accepted
26 Mar 2014
First published
27 Mar 2014

Polym. Chem., 2014,5, 3876-3883
Article type
Paper
Author version available

Multiblock sequence-controlled glycopolymers via Cu(0)-LRP following efficient thiol–halogen, thiol–epoxy and CuAAC reactions

Q. Zhang, A. Anastasaki, G. Li, A. J. Haddleton, P. Wilson and D. M. Haddleton, Polym. Chem., 2014, 5, 3876
DOI: 10.1039/C4PY00320A

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