Synthesis of Phenol-Hydrazide-Appended Tetraphenylethenes as Novel On-Off-On Cascade Sensors of Copper and Glutathione

This study reports the synthesis of novel fluorescent probes, phenol-hydrazide-appended tetraphenylethenes (TPEs I and II), and explores their photochemical properties. The probes exhibit aggregation-induced emission (AIE) in increasing water content, as observed using fluorescence spectroscopy. Further investigation with UV-vis and fluorescence techniques revealed their potential as ion sensors. Both TPE I and TPE II act as "turn-off" sensors for Cu2+ ions, showing decreased fluorescence intensity in their presence. Their limit of detection (LOD) and association constant (K-a) for Cu2+ were found to be comparable at 747 nM/597 nM, and 2.46 x 10(5) M-1/2/1.78 x 10(5) M-1/2, respectively. Moreover, the quantum yields of TPE I and TPE II were also calculated and found to be 0.651 and 0.325, respectively. Interestingly, these probes also function as "turn-on" sensors for glutathione (GSH) in the presence of copper. This means their fluorescence can be reversibly switched off and on by alternating CuCl2 and GSH additions. Moreover, the LOD values for GSH with TPE II-Cu2+ were calculated to be 544 nM. In addition, the investigation also employed visual analysis to assess the color alterations of TPEs on filter paper and in real water samples. Overall, this research introduces promising new probes with potential applications in copper ion detection and biomolecule glutathione sensing in real water samples.