1-Heteroaromatic-Substituted Tetraphenylboroles: Ï€–Ï€ Interactions Between Aromatic and Antiaromatic Rings Through a B–C Bond
By Braunschweig, Holger; Damme, Alexander; Jimenez-Halla, J. Oscar C.; Hörl, Christian; Krummenacher, Ivo; Kupfer, Thomas; Mailider, Lisa & Radacki, Krzysztof
Published in Journal of the American Chemical Society
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2012
Abstract
A series of 2,3,4,5-tetraphenylboroles substituted with different aromatic heterocycles (thiophene, furan, pyrrole, and dithiophene) in the 1-position were synthesized and characterized by means of NMR, elemental analysis, and X-ray crystallography. In contrast to known 2,3,4,5-tetraphenylboroles, X-ray diffraction revealed a nearly coplanar arrangement of the aromatic heterocycles and the antiaromatic borole scaffold as a result of π-conjugation, which could be substantiated by DFT calculations. Furthermore, the 2,2'-dithiophene-bridged bisborole (14) exhibits a large bathochromic shift in the absorption spectrum, demonstrating the exceptional Lewis acidity of the nonannulated borolyl moiety.
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