Substituent Effects on Fluorescence Properties of AIEgens Based on Coumarin-3-formylhydrazone and their Application in Cell Imaging

AIE-active compounds have lately attracted considerable attention owing to their versatile applications, especially in OLED and bioimaging. Herein, a series of coumarin-3-formylhydrazone derivatives (CFH-1, 2, 3 and 4) were developed for investigating their AIE and solid-state luminescence behaviors. All the obtained compounds emit varying degrees of solid-state fluorescence. CFH-1 and 2 show the typical AIE characteristics, while CFH-3 and 4 exhibit stronger solution fluorescence than their aggregation-induced emission. The single crystal X-ray diffraction analysis of CFH-1 and CFH-3 showed that both of them adopt planar conformation and the CH···O hydrogen bonding plays a crucial role in their crystal packing. Meanwhile, there is a notable difference between them. Successive π-π stacking interaction was observed in the crystal packing of CFH-1, while the crystals of CFH-3 contain dimeric π-π stacking interaction. Their distinct crystal packing interactions result in their different fluorescence properties. Moreover, both CFH-1 and CFH-2 displayed excellent bioimaging performances in living cells.