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

Abstract

A series of chalcogen-containing carborane derivatives were synthesized through a one-pot reaction. The nonconjugated six-membered ring of carborane-fused disulfide (<b>1</b>) can be electrochemically reduced to a dithiolate derivative. The five-membered ring of carborane-fused chalcogenophenes (<b>2</b>-<b>4</b>) showed aromaticity and considerable σ-π conjugation. The dicarborane chalcogenides (<b>5</b>-<b>7</b>) 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.