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1-Heteroaromatic-substituted tetraphenylboroles: π-π interactions between aromatic and antiaromatic rings through a
Holger Braunschweig1, Alexander Damme, J Oscar C Jimenez-Halla
1Institut für Anorganische Chemie, Julius-Maximilians Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany. h.braunschweig@uni-wuerzburg.de
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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