Side-chain modification and "grafting onto" via olefin cross-metathesis

Lucas Montero De Espinosa, Kristian Kempe, Ulrich S. Schubert, Richard Hoogenboom, Michael A R Meier

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

Olefin cross-metathesis is introduced as a versatile polymer side-chain modification technique. The reaction of a poly(2-oxazoline) featuring terminal double bonds in the side chains with a variety of functional acrylates has been successfully performed in the presence of Hoveyda-Grubbs second-generation catalyst. Self-metathesis, which would lead to polymer-polymer coupling, can be avoided by using an excess of the cross-metathesis partner and a catalyst loading of 5 mol%. The results suggest that bulky acrylates reduce chain-chain coupling due to self-metathesis. Moreover, different functional groups such as alkyl chains, hydroxyl, and allyl acetate groups, as well as an oligomeric poly(ethylene glycol) and a perfluorinated alkyl chain have been grafted with quantitative conversions. Olefin cross-metathesis (CM) enables an efficient side-chain functionalization of polymers having terminal alkenes as pendant groups. Acrylates and cis-2-butene-1,4-diacetate are used as CM partners to introduce a variety of functional groups. The scope and limitations of this polymer functionalization technique are discussed.

Original languageEnglish
Pages (from-to)2023-2028
Number of pages6
JournalMacromolecular Rapid Communications
Volume33
Issue number23
DOIs
Publication statusPublished - 13 Dec 2012
Externally publishedYes

Keywords

  • cross-metathesis
  • functionalization of polymers
  • graft copolymers
  • poly(2-oxazoline)

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