N-Heterocycle-Substituted Hexa-peri-Hexabenzocoronenes with Windmill Architectures.

We describe the synthesis and computational investigation of N-heterocycle-substituted hexa-peri-hexabenzocoronenes (HBCs). Following our method for the preparation of thioether-substituted HBCs, we prepared pyrrole-, indole-, carbazole-, and 1H-benz[g]indole-substituted HBCs from the corresponding fluorinated precursors under microwave irradiation. A series of polysubstituted benzoindole-HBCs with windmill architectures was also synthesized using the polyfluorinated HBC analogs, and the substituent effects on the electronic properties of the HBC core were investigated.