Issue 23, 2022

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
31 Mar 2022
Accepted
17 May 2022
First published
26 May 2022
This article is Open Access
Creative Commons BY-NC license

Polym. Chem., 2022,13, 3471-3478

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

C. Chen, Y. Gnanou and X. Feng, Polym. Chem., 2022, 13, 3471 DOI: 10.1039/D2PY00405D

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