J. Dosso, F. Fasano, D. Marinelli, N. Biot, A. Fermi, J. Tasseroul, D. Bonifazi
Angew. Chemie Int. Ed. 2017, 56, 4483–4487.
The first rational synthesis of a BN-doped coronene derivative in which the central benzene ring has been replaced by a borazine core is described. This includes six C−C ring-closure steps that, through intramolecular Friedel–Crafts-type reactions, allow the stepwise planarization of the hexaarylborazine precursor. UV/Vis absorption, emission, and electrochemical investigations show that the introduction of the central BN core induces a dramatic widening of the HOMO–LUMO gap and an enhancement of the blue-shifted emissive properties with respect to its all-carbon congener.