Impacts of Stereoisomerism on Molecular Packing and Charge Transport of Imide-Fused Corannulene Derivatives

Two chiral tertiary carbon centers bearing one mesityl group at each center are introduced into the molecular backbone of imide-fused corannulene derivatives to produce four stereoisomers (i.e., (S, S), (R, R), (R, S), or (S, R) configurations on two chiral carbons) in one pot, which are separated into two portions through column chromatography over silica gel. Portion 1, containing a pair of enantiomers ((S, S) and (R, R)), adopts layered packing in the crystal. Portion 2, consisting of a pair of mesomers ((R, S) and (S, R)), exhibits columnar packing in their cocrystal. Theoretical calculations are performed on these two packing motifs, revealing that Portion 1 displays hole-dominated transport, whereas Portion 2 shows electron-dominated transport.