Combining oxyanionic polymerization and click-chemistry: A general strategy for the synthesis of polyether polyol macromonomers

Anja Thomas, Kerstin Niederer, Frederik Wurm, Holger Frey*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

18 Citations (Scopus)

Abstract

We describe a synthetic pathway to tailor-made amphiphilic macromonomers by a combination of anionic ring-opening polymerization and copper-catalyzed azide-alkyne cycloaddition (CuAAC). Linear polyglycerol and poly(glyceryl glycerol) were synthesized in a controlled manner by anionic ring-opening polymerization of ethoxyethyl glycidyl ether or isopropylidene glyceryl glycidyl ether, respectively, with narrow and monomodal molecular weight distributions (Mw/Mn < 1.20) and molecular weights ranging from 850 g mol-1 to 2500 g mol-1. After end-capping with propargyl bromide and removal of the protecting groups, the hydrophilic precursors were quantitatively clicked to a series of hydrophobic azido alkyl methacrylates by copper-catalyzed azide-alkyne cycloaddition obtaining well-defined macromonomers with adjustable amphiphilic properties. Radical polymerization of these amphiphiles afforded graft copolymers with molecular weights up to 470000 g mol-1 (SEC-MALLS in DMF).

Original languageEnglish
Pages (from-to)899-909
Number of pages11
JournalPolymer chemistry
Volume5
Issue number3
DOIs
Publication statusPublished - 7 Feb 2014
Externally publishedYes

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