Synthesis and Optoelectronic Properties of Hexa-peri-hexabenzoborazinocoronene

Jacopo Dosso; Jonathan Tasseroul; Francesco Fasano; Davide Marinelli; Nicolas Biot; Andrea Fermi; Davide Bonifazi

doi:10.1002/anie.201700907

Synthesis and Optoelectronic Properties of Hexa-peri-hexabenzoborazinocoronene

Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4483-4487. doi: 10.1002/anie.201700907. Epub 2017 Mar 21.

Authors

Jacopo Dosso¹, Jonathan Tasseroul², Francesco Fasano¹, Davide Marinelli¹, Nicolas Biot¹, Andrea Fermi¹, Davide Bonifazi^{1

2}

Affiliations

¹ School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
² Department of Chemistry, University of Namur (UNamur), Rue de Bruxelles 61, Namur, 5000, Belgium.

PMID: 28323375
DOI: 10.1002/anie.201700907

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The first rational synthesis of a BN-doped coronene derivative in which the central benzene ring has been replaced by a borazine core is described.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.

Keywords: borazine; boron nitrides; heteroatom doping; hexabenzocoronenes; polycyclic aromatic hydrocarbons.

Publication types

Research Support, Non-U.S. Gov't