Electron-Deficient Contorted Polycyclic Aromatic Hydrocarbon via One-Pot Annulative π‑Extension of Perylene Diimide

The synthesis of a class of contorted electron-deficient polycyclic aromatic hydrocarbons (PAHs) has been achieved by a one-pot bay annulation of perylene diimide involving a mild Suzuki coupling and subsequent air-mediated, ambient-light-induced photocyclization. X-ray crystallography unambiguously confirmed the contorted PAH structure bearing four imide groups. The photophysical and electronic properties of these contorted PAHs were also analyzed, showing a high fluorescence quantum yield of 86% and moderate electron mobility of 0.017 cm2 V–1 s–1.