Enantiopure C5 Pentaindenocorannulenes: Chiral Graphenoid Materials

Abstract

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 C₅ 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.

Keywords: absolute configuration; buckybowls; chirality; pentaindenocorannulene.