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Pure Appl. Chem., 2012, Vol. 84, No. 4, pp. 1047-1067

Published online 2012-03-13

Hexa-peri-hexabenzocoronene in organic electronics

Helga Seyler, Balaji Purushothaman, David J. Jones, Andrew B. Holmes and Wallace W. H. Wong*

School of Chemistry, Bio21 Institute, University of Melbourne, 30 Flemington Road, Parkville, Victoria 3010, Australia

Abstract: Polycyclic aromatic hydrocarbons (PAHs) are in a class of functional organic compounds with increasing importance in organic electronics. Their tunable photophysical properties and typically strong intermolecular associations make them ideal materials in applications where control of charge mobility is essential. Hexa-peri-hexabenzocoronene (HBC) is a disc-shaped PAH that self-associates into columnar stacks through strong π–π interactions. By decorating the periphery of the HBC molecule with various substituents, a range of properties and functions can be obtained including solution processability, liquid crystallinity, and semiconductivity. In this review article, the synthesis, properties, and functions of HBC derivatives are presented with focus on work published in the last five years.