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A Pentacoordinate Boron-Containing π-Electron System with Cl–B–Cl Three-Center Four-Electron Bonds
- Dou, Chuandong, Saito, Shohei, Yamaguchi, Shigehiro
- Journal of the American Chemical Society 2013 v.135 no.25 pp. 9346-9349
- boron, electrochemistry, fluorescence
- Tricoordinate boron-containing π-electron systems are an attractive class of compounds with intense fluorescence and strong electron-accepting properties. However, the impact of pentacoordination of the boron atoms on their properties has not been determined. We now disclose a B,B′-bis(1,8-dichloro-9-anthryl)-substituted 9,10-dihydro-9,10-diboraanthracene as a new pentacoordinate organoboron compound. In this skeleton, with the aid of the orthogonal arrangement of the anthryl substituent, the B and Cl atoms can form a three-center four-electron (3c–4e) Cl–B–Cl bond. The pentacoordination of the boron atom significantly perturbs the electronic structure and thereby the photophysical and electrochemical properties.