Abstract
Imine compounds (Schiff base) have been reported with aggregation-induced emission (AIE)/aggregation-induced emission enhancement (AIEE) characteristics: they were weakly or non-emissive when dissolved well in organic solvents while the fluorescence emission turned on drastically in the presence of water. However, for some of the Schiff bases, the enhanced emission upon aggregation is derived from their parent aldehydes rather than the Schiff base molecule themselves due to the hydrolysis. The susceptibility to hydrolysis has thus limited the wide application of Schiff bases in aqueous media. In this work, a water-stable Schiff base fluorophore DBSFCN was synthesized in which the triphenylamine (TPA) electron donor and benzonitrile electron acceptor were joined together by the imine structure. The hydrolytic stability of DBSFCN was confirmed by structural and spectral analysis. Meanwhile, DBSFCN displayed significant fluorescence emission enhancement in a water/tetrahydrofuran (THF) mixture with high water content and relatively good fluorescence quantum yield at the solid state (0.48), which exhibited a typical AIEE feature. Based on the water stability and AIEE characteristic of DBSFCN, a quantitative method for the determination of water content and kinematic viscosity of the automobile brake fluid was established. In addition, DBSFCN was available in living cell imaging and reversible mechanofluorochromism.
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