Enantiopure C-5 Pentaindenocorannulenes: Chiral Graphenoid Materials

Chiral carbon nanomaterials offer numerous prospects for material science. As a fundamental building block for non-planar graphenoid materials, pentaindenocorannulene (PIC) with its C-5v symmetrical structure presents a platform for creation of supramolecular chiral carbon materials. Specifically, when uniformly penta-substituted on its periphery, PIC generates C-5 symmetrical chiral buckybowls capable of columnar stacking. The synthesis and resolution of such PICs are achieved, assignment of absolute configuration is established by comparison of ECD and VCD spectra with theory, and material characterization is reported. Evidence for columnar stacking in solution and in the crystal is presented.