π−π Interactions and Solid State Packing Trends of Polycyclic Aromatic Bowls in the Indenocorannulene Family: Predicting Potentially Useful Bulk Properties

Solid state crystal structures are discussed and compared for all seven members of the indenocorannulene family that have been recently synthesized by iterative microwave-assisted intramolecular arylations and characterized by single crystal X-ray diffraction. These bowl-shaped polyaromatic hydrocarbons include monoindenocorannulene (C26H12), two isomers each of diindenocorannulene (C32H14) and triindenocorannulene (C38H16), tetraindenocorannulene (C44H18), and pentaindenocorannulene (C50H20), with all molecules mapping onto the geodesic framework of the C60-fullerene. This extended family of π-bowls represents a unique case of a stepwise build-up of size, curvature, and strain at the corannulene core. It allows the first evaluation of the effects of controlled extension of nonplanar π-aromatic surfaces on the solid state structures of the resulting crystalline solids. First, a face-to-face π−π alignment of individual bowls to form 1D stacks is considered and compared for all the above indenocorannulenes ...