A “Turn-Off” Pyrene-Based Ligand As a Fluorescent Sensor for the Detection of Cu2+ and Fe2+ Ions: Synthesis and Application in Real Water Samples, Logic Gate Construction, and Bio-Imaging

Herein, we report the synthesis and characterization of a novel Schiff base ligand, (Z)-5-((pyren-1-ylmethylene)amino)-2,4-dihydro-3H-pyrazol-3-one (PMDP). The characterization of ligand PMDP was carried out using ESI-MS, 1H NMR, and UV–Visible spectroscopic techniques. As a probe, PMDP displayed a detectable, colorimetric colour shift in the presence of Cu2+ and Fe2+ ions. The solution was seen to have a light brown colour and to exhibit a fluorometric “turn off” response when Cu2+ and Fe2+ ions were present in a DMSO solution (HEPES 0.01 M, pH = 7.4) at room temperature. Job’s plot revealed that the PMDP binding ratio to Cu2+ and Fe2+ ions was in 1:2 ratio. In contrast to the other metal ions (Cd2+, Mn2+, Co2+, Na+, Ni2+, Cu+, Fe3+, Hg2+, Mg2+, Zn2+, K+, and V5+), the synthesised probe showed exceptional sensitivity and selectivity for detecting Cu2+ and Fe2+ metal ions. The results indicate that the detection limits for Cu2+ and Fe2+ are 0.42 μM and 0.51 μM, respectively. Furthermore, PMDP was efficiently utilised for the quantitative analysis of Cu2+ and Fe2+ in real water samples, RGB colour values in smart phones, logic gate construction, and cell imaging in HeLa cells.