General Method for the Synthesis of Functionalized Tetrabenzo[8]circulenes

Functionalized derivatives of the saddle-shaped molecule tetrabenzo[8]­circulene were successfully synthesized through a Diels–Alder/oxidative cyclodehydrogenation approach. This methodology improves on our previously reported synthesis, affording products containing both electron-rich and electron-poor functional groups from readily available starting materials in a more efficient manner. The optoelectronic effects that result from the introduction of this functionality are presented and briefly discussed.