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

Abstract

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

ortho O-Annulated azabenzannulated perylenediimide and bisazacoronenediimide

“…The inclusion of oxygen atoms 6 in the skeleton of PAHs leads to applications ranging from chiroptics 7 and spintronics 8 to organic electronics 9 and photocatalysis. 10 Bonifazi and co-workers 11 have extensively studied the synthesis and properties of oxygen-doped PAHs resulting in a collection of functional conjugated systems for electrochromic displays, 12 photocatalysis, 13 charge transport, 14 and nonlinear optics. 15 These oxygen-doped PAHs are prepared through copper-catalysed oxidative C–H activation of hydroxy-decorated PAHs precursors.…”