An expanded rosarian (P3P6) with a bowl like conformation has been prepared and characterized in a one-pot procedure that involves condensing a bispyrrole pyridine precursor (P-1,P-2) with benzaldehyde, followed by oxidation. Single crystal X-ray diffraction analysis reveals a bowl-like conformation in the solid state with an upper rim diameter defined by the meso-phenyl substituents of ca. 13.5 angstrom and a depth of roughly 6.3 angstrom. P3P6 forms both 1:1 and 2:1 complexes with C-60 in the solid state. DFT reveals similar energies for the two binding modes. A 1:1 binding stoichiometry dominates in 1,2-dichlorobenzene-d(4) at the millimolar concentrations dictated by solubility consideration. The solution phase interactions between rosarian and C60 were studied using H-1 NMR, UV vis, and femtosecond transient absorption spectroscopies in 1,2-ichlorobenzene-d(4) or toluene. To our knowledge, this is the first report of an unfunctionalized porphyrinoid that forms a well-defined complex with C-60 in solution as well as in solid state.