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A Pentacoordinate Boron-Containing π-Electron System with Cl–B–Cl Three-Center Four-Electron Bonds

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Institute of Transformative Bio-Molecules (WPI-ITbM), Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602, Japan
[email protected]
Cite this: J. Am. Chem. Soc. 2013, 135, 25, 9346–9349
Publication Date (Web):June 10, 2013
https://doi.org/10.1021/ja404724f
Copyright © 2013 American Chemical Society
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    Abstract

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    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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    Experimental procedures, crystallographic data (CIF) for 4Cl and 5, photophysical properties, theoretical calculations, and complete ref 16 (as ref S4). This material is available free of charge via the Internet at http://pubs.acs.org. The supplementary crystallographic data for 4Cl (CCDC-924601) and 5 (CCDC-924602) have also been deposited with the Cambridge Crystallographic Data Centre.

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