Photocontrolled Radical Polymerization from Hydridic C-H Bonds

Erin E. Stache, Veronika Kottisch, Brett P. Fors

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

Given the ubiquity of carbon-hydrogen bonds in biomolecules and polymer backbones, the development of a photocontrolled polymerization selectively grafting from a C-H bond represents a powerful strategy for polymer conjugation. This approach would circumvent the need for complex synthetic pathways currently used to introduce functionality at a polymer chain end. On this basis, we developed a hydrogen-atom abstraction strategy that allows for a controlled polymerization selectively from a hydridic C-H bond using a benzophenone photocatalyst, a trithiocarbonate-derived disulfide, and visible light. We performed the polymerization from a variety of ethers, alkanes, unactivated C-H bonds, and alcohols. Our method lends itself to photocontrol which has important implications for building advanced macromolecular architectures. Finally, we demonstrate that we can graft polymer chains controllably from poly(ethylene glycol) showcasing the potential application of this method for controlled grafting from C-H bonds of commodity polymers.

Original languageEnglish (US)
Pages (from-to)4581-4585
Number of pages5
JournalJournal of the American Chemical Society
Volume142
Issue number10
DOIs
StatePublished - Mar 11 2020
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Photocontrolled Radical Polymerization from Hydridic C-H Bonds'. Together they form a unique fingerprint.

Cite this