Dual-reactive hyperbranched polymer synthesis through proton transfer polymerization of thiol and epoxide groups

Ikhlas Gadwal, Selmar Binder, Mihaiela C. Stuparu, Anzar Khan

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

A new synthesis of hyperbranched polymers through proton transfer polymerization of thiol and epoxide groups is presented. For this, an AB 2 monomer bearing two epoxides and a thiol groups is synthesized. Base-catalyzed proton transfer polymerization of this monomer led to the formation of a polythioether-based hyperbranched polymer with a 65-69% degree of branching and carrying about 2% of disulfide-based structural defects. This polymer contained two reactive sites, a hydroxyl group and an epoxide unit, distributed throughout the branched scaffold. The epoxide groups could be employed in anchoring an alkyl, aryl, or ethylene oxide chain through a thiol-epoxy reaction, while the hydroxyl groups produced during the polymerization and the first functionalization reactions could be engaged in attaching positively charged primary ammonium groups to the branched backbone. These sequential postpolymerization modifications transformed the general dual-reactive scaffold into dual-functionalized hyperbranched materials with potential utility in the arena of gene delivery applications.

Original languageEnglish
Pages (from-to)5070-5080
Number of pages11
JournalMacromolecules
Volume47
Issue number15
DOIs
Publication statusPublished - 2014 Aug 12
Externally publishedYes

Fingerprint

Functional polymers
Proton transfer
Epoxy Compounds
Sulfhydryl Compounds
Polymerization
Scaffolds
Polymers
Bearings (structural)
Monomers
Hydroxyl Radical
Ethylene Oxide
Ethylene
Genes
Ammonium Compounds
Disulfides
Defects
Oxides

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Dual-reactive hyperbranched polymer synthesis through proton transfer polymerization of thiol and epoxide groups. / Gadwal, Ikhlas; Binder, Selmar; Stuparu, Mihaiela C.; Khan, Anzar.

In: Macromolecules, Vol. 47, No. 15, 12.08.2014, p. 5070-5080.

Research output: Contribution to journalArticle

Gadwal, Ikhlas ; Binder, Selmar ; Stuparu, Mihaiela C. ; Khan, Anzar. / Dual-reactive hyperbranched polymer synthesis through proton transfer polymerization of thiol and epoxide groups. In: Macromolecules. 2014 ; Vol. 47, No. 15. pp. 5070-5080.
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