A Silicon-Doped Nanographenic Bowl for Supramolecular Assembly with Fullerenes

A silicon-doped nanographenic bowl, trisilasupersumanene 1, was synthesized via a 3-fold palladium-catalyzed sila-annulation from the hexachlorinated trifluorenocoronene. Incorporating silole rings into the aromatic framework leads to new reduction waves in cyclic voltammetry and low-lying LUMO levels. The bowl 1 exhibits high binding affinity to fullerenes C 60 and C 70, forming supramolecular complexes 1⊃C 60 and (1) 2 ⊃C 70 with unique packing arrangements. Notably, (1) 2 ⊃C 70 features a rare clam-like structure in the crystal, entirely different from its binding behavior in solution.