HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

A series of novel O-doped polycyclic aromatic hydrocarbons, bearing a different number electron-donating alkoxy substituents, has been prepared using copper-promoted anaerobic protocol for the cyclisation highly electron rich peri-xanthenoxanthene molecular modules. The effect and position substituents on optoelectronic properties thus investigated, unveiling p-type semiconducting properties. All molecules displayed significant colour change upon oxidation, suggesting that these compounds can be used to devise chromogenic materials engineer electrochromic devices.