Gram-scale synthesis and crystal structures of [8]- and [10]CPP, and the solid-state structure of C-60@[10]CPP

A cost-effective gram-scale synthesis of [8]- and [10]cycloparaphenylenes (CPPs) has been developed for the first time. Both [8]- and [10]cycloparaphenylene organized into herringbone geometries in the crystalline state with well-defined cylindrical cavities of 1.1 and 1.4 nm, respectively. With large amounts of material available, the highly efficient convex-concave pi-pi interactions between [10]CPP and C-60 in the solid-state was validated by X-ray diffraction analysis.