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Synfacts 2020; 16(03): 0288
DOI: 10.1055/s-0039-1690376
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Oxygen/Sulfur Exchange in Epoxides to Make Poly(thioethers)

Contributor(s):
Timothy M. Swager
,
Alberto Concellón
Zhang C.-J, Zhang X.-H. * Zhejiang University, Hangzhou, P. R. of China
Chemoselective Coupling of CS2 and Epoxides for Producing Poly(thioether)s and COS via Oxygen/Sulfur Atom Exchange.

Macromolecules 2020;
53: 233-239
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Further Information

Publication History

Publication Date:
18 February 2020 (online)

 
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Key words

acid-promoted ring-closing - conjugated polymers - polycyclic aromatic hydrocarbons

Significance

Poly(thioether)s are interesting sulfur-rich polymers that may display enhanced properties in comparison with their sulfur-free counterparts. Despite their promising applications in biomedicine and energy materials, there is still not a robust method for producing poly(thioether)s from readily available monomers. Herein, the authors developed a new, versatile approach to access poly(thioether)s from epoxides and carbon disulfide (CS2), a low-cost sulfur-rich feedstock.


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Comment

The sulfur atom of CS2 is one-to-one exchanged with the oxygen atom of epoxide, leading to the formation of carbonyl sulfide (COS) and episulfide that can be further polymerized to form different poly(thioether)s in up to 10 g in one batch. This reaction can be conducted in air at 120 °C with several organic bases as initiator and extended to a variety of epoxides. Future research on this promising method should focus on the development of new catalytic systems that allow better control of the polymerization to obtain poly(thioether)s with higher molecular weights.


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