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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. [ABSTRACT FROM AUTHOR]

A series of 3-aroylbenzocoumarin-based luminogens have been synthesized for investigating their aggregation-induced emission (AIE) and solid-state fluorescence. The single crystal X-ray diffraction analysis of one of them showed that the molecules are arranged in the form of π-dimers which may lead to excimer emission. The large Stokes shifts and the broad-band emission of these 3-aroylbenzocoumarins in solid/aggregation state demonstrated the probable formation of excimers. The shapes of benzocoumarin units have a great effect on the AIE behaviors. The linear benzocoumarin derivatives show larger Stokes shifts, while the bent-benzocoumarin derivatives exhibit better AIE performances. All of them show aggregation-enhanced excimer emission which is supported by the large Stokes shifts. The electronic effect of 3-aroyl groups also has a certain effect on their fluorescence properties. The polymorphism phenomenon was observed for one of the benzoyl-containing derivatives. Additionally, two of the derivatives containing methoxy group were successfully used for cell imaging. [ABSTRACT FROM AUTHOR]