The first rational synthesis of a BN-doped coronene derivative in which the central benzene ring has been replaced by a borazine core is described.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.
Dosso J., Tasseroul J., Fasano F., Marinelli D., Biot N., Fermi A., et al. (2017). Synthesis and Optoelectronic Properties of Hexa-peri-hexabenzoborazinocoronene. ANGEWANDTE CHEMIE. INTERNATIONAL EDITION, 56(16), 4483-4487 [10.1002/anie.201700907].
Synthesis and Optoelectronic Properties of Hexa-peri-hexabenzoborazinocoronene
Fermi A.;
2017
Abstract
The first rational synthesis of a BN-doped coronene derivative in which the central benzene ring has been replaced by a borazine core is described.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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
