The Synthesis And Performance Of Hydrazone Derivatives With Aggregation-induced Emission Properties

In this paper, a series of hydrazone derivatives were designed and synthesized, including eight kinds of V-shaped D-π-A-π-D compounds with sulfone centre and three kinds of compounds with triphenylamine centre. Their structures were characterized by NMR, IR, and element analysis. Then, we explore the luminescent behaviour of the prepared derivatives and studied their applications. AIE test suggested the enhanced fluorescence in the aggregation state and its high fluorescence quantum yield. Meanwhile, the fluorescence microscope exhibited the strong fluorescence of the aggregation directly. The SEM image revealed the nanoscaled appearance of BAHDS and DHS derivatives. We also studied the reason of the high AIE effect of BAHDS and DHS derivatives with the molecular dynamic calculation. The calculation result introduced the packing modes of these compounds. It suggested that intermolecular hydrogen bond, special intermolecular force and other reasons inhibited the intramolecular rotation, which caused AIE effect. We also found high fluorescent quantum yield of three TPAS derivatives in THF solution and THF/water mixture solution. The maximum emission wavelength of TPAS-3 aggregrations in THF/water mixture solution red shifted because of the solvation effect. Finally, living cell imaging was performed and it considered that BAHDS and DHS derivatives had good cell permeability and low cyclotoxity. It was successfully applied to living cells staining, which demonstrated its value for practical applications in physiological systems.