PEG-based multifunctional polyethers with highly reactive vinyl-ether side chains for click-type functionalization

Christine Mangold, Carsten Dingels, Boris Obermeier, Holger Frey*, Frederik Wurm*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

56 Citations (Scopus)

Abstract

Introduction of highly reactive vinyl ether moieties along a poly(ethylene glycol) (PEG) backbone has been realized by copolymerization of the novel epoxide monomer ethoxy vinyl glycidyl ether (EVGE) with ethylene oxide (EO). A series of copolymers with varying structure (block and random) as well as EVGE comonomer content (5-100%) with molecular weights in the range of 3,900-13,200 g/mol and narrow molecular weight distributions (Mw/Mn = 1.06-1.20) has been synthesized and characterized with respect to their microstructure and thermal properties. The facile transformation of the vinyl ether side chains in click type reactions was verified by two different post polymerization modification reactions: (i) thiol-ene addition and (ii) acetal formation, employing various model compounds. Both strategies are very efficient, resulting in quantitative conversion. The rapid and complete acetal formation with alcohols results in an acid-labile bond and is thus highly interesting with respect to biomedical applications that require slow or controlled release of a drug, while the thiol-ene addition to a vinyl ether prevents cross-linking efficiently compared to other double bonds.

Original languageEnglish
Pages (from-to)6326-6334
Number of pages9
JournalMacromolecules
Volume44
Issue number16
DOIs
Publication statusPublished - 23 Aug 2011
Externally publishedYes

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