Cycloparaphenylene Double Nanohoop: Structure, Lamellar Packing, and Encapsulation of C60 in the Solid State.

A new member of the cycloparaphenylene double-nanohoop family was synthesized. Its π-framework features two oval cavities that display different shapes depending on the crystallization conditions. Incorporation of the peropyrene bridge within the nanoring cycles via bay-regions alleviates steric effects and thus allows 1:1 complexation with C60 in the solid state. This nanocarbon adopts a lamellar packing motif, and our results suggest that the structural adjustment of this double nanohoop could enable its use in supramolecular and semiconductive materials.