New Synthetic Routes to <i>Z</i>-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.