Organocatalytic selective coupling of episulfides with carbon disulfide for the synthesis of poly(trithiocarbonate)s and cyclic trithiocarbonates

Chao Chen, Yves Gnanou, Xiaoshuang Feng

Research output: Contribution to journalArticlepeer-review

Abstract

This work reports how to efficiently utilize carbon disulfide (CS2) as a sulfur-containing C1 resource for the purpose of synthesizing both linear poly(trithiocarbonate)s and cyclic trithiocarbonates. When initiated by PPNCl or phosphazene benzoxide, the copolymerization of CS2 with episulfides affords perfectly alternating poly(trithiocarbonate)s in the absence of any catalyst. In contrast, when initiated by tetrabutylammonium halide, the same coupling reaction of CS2 with episulfides results in the formation of cyclic trithiocarbonates. The role played by initiating onium salts in the linear/cyclic selectivity as well as reaction conditions such as the temperature, the type of solvent, and the feeding ratio of CS2 to episulfides was investigated. Lastly, when placed in the presence of a radical source or treated with UV irradiation, poly(trithiocarbonate)s undergo complete unzipping to produce cyclic trithiocarbonates. This remarkable feature has been harnessed to prepare degradable polymers using oligotrithiocarbonates as self-immolating linkers between dithiol alkyl precursors.
Original languageEnglish (US)
JournalPolymer Chemistry
DOIs
StatePublished - May 26 2022

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Biomedical Engineering
  • Bioengineering
  • Polymers and Plastics

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