Hexa-peri-hexabenzocoronenes – Controlling their Self-Assembly by Engineering the Lateral Substituents

Abstract

Polycondensed aromatic hydrocarbons (PAH), which can be regarded as two-dimensional subsections of graphite, have begun to attract increasing interest in supramolecular chemistry. Substituted hexa-peri-hexabenzocoronenes (HBC), an outstanding class of PAH, are well-known to self-organize in solution into highly ordered columnar molecular stacks. The formed structures are very sensitive to any variation of the medium as well as the lateral substituents of the HBC derivatives. Various perfluoroalkylated HBC compounds have been prepared and investigated by powder XRD, DSC, fluorescence and cryo-SEM in order to gain certain control over the self-assembling behavior of this class of compounds.