X-Shaped Polycyclic Aromatic Hydrocarbons: Optical Properties and Tunable Assembly Ability

Although a number of synthetic methodologies have been developed to prepare stable polycyclic aromatic hydrocarbons (PAHs), much less research has been devoted to functionalizing the peripheries of molecules to tune the self-assembly ability or introduce functional groups without altering their photophysical properties. Herein, we report twisted "X"-shaped molecules prepared through annulation of hexacene with benzoanthracene on the zigzag edge, and an investigation of their photophysical properties and self-assembly properties. The shape-complementary "X"-shaped molecules prefer to dimerize, while the π-extension would lead to one-dimensional π-stacking. Our findings give some insights into the design of stable PAHs without disturbing the electronic structures.