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

Sarah Tempelaar, Ian A Barker, Vinh Xuan Truong, Daniel J Hall, Laetitia Mespouille, Philippe Dubois, Andrew P Dove

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42 Citations (Scopus)

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
Original languageEnglish
Pages (from-to)174 - 183
Number of pages10
JournalPolymer Chemistry
Volume4
Issue number1
DOIs
Publication statusPublished - 2013
Externally publishedYes

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