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J Am Chem Soc. 2013 Jun 26;135(25):9346-9. doi: 10.1021/ja404724f. Epub 2013 Jun 13.

A pentacoordinate boron-containing π-electron system with Cl-B-Cl three-center four-electron bonds.

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  • 1Institute of Transformative Bio-Molecules (WPI-ITbM), Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602, Japan.


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.

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