A novel triphenylamine-based bis-Schiff bases fluorophores with AIE-Activity as the hydrazine fluorescence turn-off probes and cell imaging in live cells

Developing a specific and sensitive method for endogenous hydrazine detection in living systems is valuable to understand its various pathological events. In this work, two novel fluorescent chemosensors (C1, C3) based on triphenylamine Schiff-base derivative and reference dyes (C2, C4) were prepared in relatively high yield (more than 72% yield). The aggregation induced emission (AIE) properties of sensors were investigated through UV-Visible, dynamic light scattering, X-ray diffraction, fluorescence spectrophotometric analyses as well as scanning electron microscope images (SEM). The results indicated that probes C1 and C3 exhibited strong AIE property in DMF/H2O (1:1, v/v) mixture system with brilliant yellow fluorescence emission (560 nm) observed under 365 nm UV lamp. The experiments of sensing indicated that probes C1 and C3 possessed the sequentially detecting abilities for hydrazine with high sensitivity, specificity as well as an extremely low detection limit (55.1 nM), which was due to blocking of AIE process of probes C1 and C3 by special chemical reaction (-CH=N- moiety transformed into -CH2-NH- group) after hydrazine addition, resulting in the increase in water solubility and a weak emission in aqueous media. Furthermore, H-1 NMR, SEM and fluorescence titration experiment was also conducted to confirm the sensing mechanism. For biological application, probes C1 and C3 presented a good bio-imaging performance and showed the similar fluorescence quenching after adding hydrazine. Therefore, the probes are suitable for the fluorescence imaging of exogenous hydrazine in HeLa cells.