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An Investigation on the Production of Random Copolymer with Monothiocarbonate and Trithiocarbonate Units over Cyclic Thiocarbonate via Metal‐free Catalysis

Jialiang Yang, Lan‐Fang Hu, Xiao‐Han Cao, Ying Wang, Xinghong Zhang

2020Chinese Journal of Chemistry24 citationsDOI

Abstract

Summary of main observation and conclusion Synthesis of poly(thiocarbonate)s from the copolymerization of epoxides and carbon disulfide (CS 2 ) remains a tough challenge, due to inevitable oxygen‐sulfur atom scrambling process. In this work, we utilized the oxygen‐sulfur exchange reaction (O‐S ER) to synthesize a random copolymer with monothiocarbonate and trithiocarbonate units from CS 2 and phenyl glycidyl ether (PGE) via metal‐free Lewis pairs. The copolymers contained monothiocarbonate and trithiocarbonate units of which the molar fraction could be tuned by varying either the types of Lewis pairs or the reaction temperature. Keeping track on the intermediate provided an insight in the process of O‐S ER and thus gave a hint to control the product structure. Production and consumption of phenyl thioglycidyl ether was the key process to regulate the chain structure. Remarkably, the oxygen atoms of PGE could be excluded out of the chain, resulting in the nearly complete production of poly(trithiocarbonate)s. Correspondingly, the refractive index of this kind of copolymer could be regulated in a wide range of 1.73—1.79 (at 590 nm).

Topics & Concepts

ChemistryCopolymerPolymer chemistryCarbon disulfideCatalysisLewis acids and basesEtherOrganic chemistryPolymerCarbon dioxide utilization in catalysisChemical Synthesis and Reactionsbiodegradable polymer synthesis and properties
An Investigation on the Production of Random Copolymer with Monothiocarbonate and Trithiocarbonate Units over Cyclic Thiocarbonate via Metal‐free Catalysis | Litcius