Synthesis and Optoelectronic Properties of Hexa-peri-hexabenzoborazinocoronene.
The first rational synthesis of a BN-doped coronene derivative in which the central benzene ring has been replaced by a borazine core is described.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.
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Jacopo
0000-0003-4173-3430
J
Dosso
Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, Namur, 5000, Belgium.
Jonathan
J
Tasseroul
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Francesco
F
Fasano
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Davide
D
Marinelli
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Nicolas
N
Biot
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Andrea
0000-0003-1080-0530
A
Fermi
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.|Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, Namur, 5000, Belgium.
Davide
0000-0001-5717-0121
D
Bonifazi
borazine; boron nitrides; heteroatom doping; hexabenzocoronenes; polycyclic aromatic hydrocarbons