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Synthesis and Optoelectronic Properties of Hexa‐ peri ‐hexabenzoborazinocoronene
Author(s) -
Dosso Jacopo,
Tasseroul Jonathan,
Fasano Francesco,
Marinelli Davide,
Biot Nicolas,
Fermi Andrea,
Bonifazi Davide
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700907
Subject(s) - intramolecular force , ring (chemistry) , annulation , chemical mechanical planarization , photochemistry , chemistry , materials science , homo/lumo , doping , absorption (acoustics) , nanotechnology , optoelectronics , stereochemistry , molecule , organic chemistry , layer (electronics) , catalysis , composite material
The first rational synthesis of a BN‐doped coronene derivative in which the central benzene ring has been replaced by a borazine core is described.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.