The Marriage of Carborane with Chalcogen Atoms: Nonconjugation, σ−π Conjugation, and Intramolecular Charge Transfer

A series of chalcogen-containing carborane derivatives were synthesized through a one-pot reaction. The nonconjugated six-membered ring of carborane-fused disulfide (1) can be electrochemically reduced to a dithiolate derivative. The five-membered ring of carborane-fused chalcogenophenes (2−4) showe...

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Bibliographic Details
Published in:Organic letters 2019-10, Vol.21 (20), p.8285-8289
Main Authors: Yang, Xiaodong, Zhang, Bingjie, Zhang, Sikun, Li, Guoping, Xu, Letian, Wang, Zhijun, Li, Pengfei, Zhang, Yanfeng, Liu, Zishun, He, Gang
Format: Article
Language:English
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Summary:A series of chalcogen-containing carborane derivatives were synthesized through a one-pot reaction. The nonconjugated six-membered ring of carborane-fused disulfide (1) can be electrochemically reduced to a dithiolate derivative. The five-membered ring of carborane-fused chalcogenophenes (2−4) showed aromaticity and considerable σ−π conjugation. The dicarborane chalcogenides (5−7) showed intramolecular charge-transfer-induced emission. These chalcogen-containing carborane derivatives provided a useful platform to study the electron interaction systematically and shed some light on the design of carborane-based optoelectronic materials.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03047