Thiol-epoxy polymerization via an AB monomer: Synthetic access to high molecular weight poly(β-hydroxythio-ether)s

Selmar Binder, Ikhlas Gadwal, Andreas Bielmann, Anzar Khan

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

A synthetic route is developed for the preparation of an AB-type of monomer carrying an epoxy and a thiol group. Base-catalyzed thiol-epoxy polymerization of this monomer gave rise to poly(β-hydroxythio-ether)s. A systematic variation in the reaction conditions suggested that tetrabutyl ammonium fluoride, lithium hydroxide, and 1,8-diazabicycloundecene (DBU) were good polymerization catalysts. Triethylamine, in contrast, required higher temperatures and excess amounts to yield polymers. THF and water could be used as polymerization mediums. However, the best results were obtained in bulk conditions. This required the use of a mechanical stirrer due to the high viscosity of the polymerization mixture. The polymers obtained from the AB monomer route exhibited significantly higher molecular weights (Mw = 47,700, Mn = 23,200 g/mol) than the materials prepared from an AA/BB type of the monomer system (Mw = 10,000, Mn = 5400 g/mol). The prepared reactive polymers could be transformed into a fluorescent or a cationic structure through postpolymerization modification of the reactive hydroxyl sites present along the polymer backbone.

Original languageEnglish
Pages (from-to)2040-2046
Number of pages7
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume52
Issue number14
DOIs
Publication statusPublished - 2014 Jul 15
Externally publishedYes

Keywords

  • addition polymerization
  • click polymerization
  • functionalization of polymers
  • polyelectrolytes
  • thiol-epoxy reaction

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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