Chiral carbon nanomaterials offer numerous prospects for material science.Asafundamental building blockfor non-planar graphenoid materials,p entaindenocorannulene (PIC) with its C 5v symmetrical structure presents ap latform 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,a ssignment 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.

Four chiral N-heterocyclic monoindenocorannulenes were prepared by fusing pyridine, quinoline, and indole across the peri-positions of corannulene via tandem Suzuki-aryl-aryl coupling and C-Cl activated ring closure reactions. The UV-Vis, fluorescence, and CV properties of these N-doped polynuclear aromatics are discussed. Resolution of enantiomers is performed on chiral stationary phase HPLC and the absolute configurations are assigned by comparison of experimental and quantum mechanically predicted ECD spectra.

Chiral carbon nanomaterials offer numerous prospects for material science.Asafundamental building blockfor non-planar graphenoid materials,p entaindenocorannulene (PIC) with its C 5v symmetrical structure presents ap latform 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,a ssignment 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.

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