Abstract
Hexa-peri-hexabenzocornene(HBC) and its derivatives have attracted long-term interest due to their high stability, their self-assembling behavior, and promising application in the fields of molecular electronics and nanotechnology. However, few studies have been reported on the unimolecular character of HBCs because of the lack of functionalization methods for HBCs. The direct conversion of C-H bonds to C-B bonds has been an active area of metal-catalyzed C-H bonds functionalization in these days. This time, we performed the direct functionalization of HBCs by iridium catalyzed C-H borylation. The reaction proceeded with high regioselectivity in high yield. This is the first example of direct functionalization of HBC periphery. Hydroxy groups were easily introduced by the oxidation with hydrogen peroxide. This product could not be synthesized through conventional methods. Oxidation of the hydoroxy group with PIFA afforded a new type of pi-extended quinone based on HBC.
