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Issue 1, 2013
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Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s

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Abstract

The synthesis of well-defined propargyl-functional poly(carbonate)s was achieved via the organocatalytic ring-opening polymerization of 5-methyl-5-propargyloxycarbonyl-1,3-dioxan-2-one (MPC) using the dual catalyst system of 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The resulting homopolymers showed low dispersities and high end-group fidelity, with the versatility of the system being demonstrated by the synthesis of telechelic copolymers and block copolymers. The synthesized homopolymers with varying degree of polymerization were functionalized with a range of azides via copper-catalyzed Huisgen-1,3-dipolar addition or thiols via radical thiylation, to produce functional aliphatic poly(carbonate)s from a single polymeric scaffold.

Graphical abstract: Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s

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Article information


Submitted
06 Sep 2012
Accepted
15 Sep 2012
First published
17 Sep 2012

Polym. Chem., 2013,4, 174-183
Article type
Paper

Organocatalytic synthesis and post-polymerization functionalization of propargyl-functional poly(carbonate)s

S. Tempelaar, I. A. Barker, V. X. Truong, D. J. Hall, L. Mespouille, P. Dubois and A. P. Dove, Polym. Chem., 2013, 4, 174
DOI: 10.1039/C2PY20718D

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