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) 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.