Synthesis, Structure, and Properties of Tetrabenzo[7]circulene.

Tetrabenzo[7]circulene, a new member of aromatic saddles, was conveniently synthesized from 2-(1-naphthoyl)benzoic acid with the seven-membered ring constructed at an early stage of the synthesis. This method, upon minor modification, was also useful for synthesis of thiophene-annulated [7]circulenes. The structures of tetrabenzo[7]circulene and [7]circulene were compared in terms of symmetry, flexibility, and curvature on the basis of DFT calculations and X-ray crystallography. It was also found that tetrabenzo[7]circulene functioned as a p-type semiconductor in thin-film transistors and cocrystallized with C60.