New synthetic routes to Z-shape functionalized perylenes.

Z-shape (1,2,7,8-tetrasubstituted) perylene derivatives are novel chromophores with great potential in various applications. Yet, the synthetic entry into this class of molecules is hitherto quite limited. In this communication, the synthesis of a series of Z-shape perylene derivatives via a double Wittig-Knoevenagel benzannulation protocol is reported. Preliminary photophysical and electrochemical studies indicate that the frontier orbital energy levels of these new perylene systems are modulated by electronic, regiochemical, and conformational effects.