Hexa-peri-hexabenzocoronene in organic electronics

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.

Synthesis and Chiroptical Properties of Hexa‐, Octa‐, and Deca‐azaborahelicenes: Influence of Helicene Size and of the Number of Boron Atoms

“…[1] Representative achiral heteroarenes are, for instance, graphene analogues doped with heteroatoms (Si, S, B, N, P). [2] Heterohelicenes, on the other hand, may be considered as chiral heteroatomic PAHs.…”

Theoretical investigation on the optoelectronic properties of non-centrosymmetric D–A–D hexaazatriphenylene derivatives for photovoltaic applications

“…aromatic hydrocarbons (PAHs, also polyaromatic hydrocarbons) are organic compounds composed of two or more fused aromatic rings with delocalized electrons. PAHs are often found naturally in combustion residues but, analytically pure and discrete PAHs are obtained only through synthesis 1 . Most PAHs are also fluorescent, emitting characteristic wavelengths of light when excited 2 .…”

Nanoscale assembly into extended and continuous structures and hybrid materials

“…40 HBCs are liquid crystals (LCs), p-stacking in solution to form columns, which may provide ideal percolation pathways for charge transport between electrodes in PV devices (Figure 3a). 41 Aliphatic chains solubilize the individual molecules and resulting structures, and dictate the LC phase transition temperature by reinforcing columnar stacking through solvophobic interactions. HBC columns exhibit excellent photoconduction (1 cm 2 V À1 s À1 ) when oxidatively doped (for example, with nitrosonium tetrafluoroborate), 42 and provide electron or hole transport in the active layer of a bulk heterojunction PV device.…”