Scalable ambient synthesis of water-soluble poly(β-hydroxythio-ether)s

Ji Hyeon Hwang, Youngson Choe, Joona Bang, Anzar Khan

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Proton transfer polymerization through thiol-epoxy “click” reaction between commercially available and hydrophilic di-thiol and di-epoxide monomers is carried out under ambient conditions to furnish water-soluble polymers. The hydrophilicity of monomers permitted use of aqueous tetrahydrofuran as the reaction medium. A high polarity of this solvent system in turn allowed for using a mild catalyst such as triethylamine for a successful polymerization process. The overall simplicity of the system translated into a simple mixing of monomers and isolation of the reactive polymers in an effortless manner and on any scale required. The structure of the resulting polymers and the extent of di-sulfide defects are studied with the help of 13C- and 1H-NMR spectroscopy. Finally, reactivity of the synthesized polymers is examined through post-polymerization modification reaction at the backbone sulfur atoms through oxidation reaction. The practicality, modularity, further functionalizability, and water solubility aspects of the described family of new poly(β-hydroxythio-ether)s is anticipated to accelerate investigations into their potential utility in bio-relevant applications.

Original languageEnglish
Pages (from-to)3381-3386
Number of pages6
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume55
Issue number20
DOIs
Publication statusPublished - 2017 Oct 15

Keywords

  • click polymerization
  • functionalization of polymers
  • step-growth polymerization
  • thiol-epoxy reaction
  • water-soluble polymers

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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