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

6 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

Fingerprint

Ether
Ethers
Polymers
Monomers
Polymerization
Sulfhydryl Compounds
Water
Functional polymers
Proton transfer
Epoxy Compounds
Hydrophilicity
Sulfides
Sulfur
Nuclear magnetic resonance spectroscopy
Solubility
Atoms
Oxidation
Defects
Catalysts
triethylamine

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

Cite this

Scalable ambient synthesis of water-soluble poly(β-hydroxythio-ether)s. / Hwang, Ji Hyeon; Choe, Youngson; Bang, Joona; Khan, Anzar.

In: Journal of Polymer Science, Part A: Polymer Chemistry, Vol. 55, No. 20, 15.10.2017, p. 3381-3386.

Research output: Contribution to journalArticle

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