Synthesis, Photoswitching Behavior and Nonlinear Optical Properties of Substituted Tribenzo[a,d,g]coronene

A family of tribenzocoronene derivatives bearing various substituents (3) were constructed through the Diels–Alder reaction, followed by the Scholl oxidation, where the molecular structure of 3b was determined via single crystal X-ray diffraction analysis. The effect of substitution on the optical and electrochemical property was systematically investigated, with the assistance of theoretical calculations. Moreover, the thin films of the resulting molecules 3b and 3e complexed with fullerene produced strong photocurrent response upon irradiation of white light. In addition, 3b and 3e exhibit a positive nonlinear optical response resulting from the two-photon absorption and excited state absorption processes.