A unique paradigm for intermolecular charge transport mediated by diffuse atomic-like orbital (SAMOs), typically present in conjugated hollow shaped molecules, is investigated for C20H10 molecular fragments by means of G0W0 theory. Inclusion of many body screening and polarization effects is seen to be important for accurate prediction of electronic properties involving these diffuse orbitals. Theoretical predictions are made for the series of bowl-shaped fullerene fragments, C20H10, C30H10, C40H10, C50H10. Interesting results are found for the LUMO-SAMO energy gap in C20H10, which is shown to be nearly an order of magnitude lower that that determined for C60. Given the ability to support bowl fragments on metal surfaces, these results suggest the concrete possibility for exploiting SAMO-mediated electron transport in supramolecular conducting layers.