Complexation of an Anthracene-Triptycene Nanocage Host with Fullerene Guests through CH⋅⋅⋅π Contacts

A bicyclic anthracene macrocycle containing two triptycene units at the bridgehead positions was synthesized by Ni-mediated coupling of the corresponding precursor as a cage-shaped aromatic hydrocarbon host. This cage host formed an inclusion complex with C₆₀ or C₇₀ guest in 1 : 1 ratio in solution. The association constants (K_a ) determined by the fluorescence titration method were 1.3×10⁴ and 3.3×10⁵  L mol ^-1 for the C₆₀ and C₇₀ complexes, respectively, at 298 K in toluene. DFT calculations revealed that the guest molecules were included in the middle of the cavity with several CH⋅⋅⋅π contacts. The strong affinity of the cage host for the fullerene guests and the high selectivity toward C₇₀ are discussed on the basis of spectroscopic and structural data.