A Highly Fluorescent Pyrene-based Sensor for Selective Detection of Fe3+ Ion in Aqueous Medium: DFT and Molecular Docking Studies

In this work, we introduce a highly selective and sensitive fluorescent sensor based on pyrene derivative for Fe(III) ion sensing in DMSO/water media. 2-(pyrene-2-yl)-1-(pyrene-2-ylmethyl)-1H-benzo[d]imidazole (PEBD) receptor was synthesized via simple condensation reaction and confirmed by spectroscopic techniques. The receptor exhibits fluorescence quenching in the presence of Fe(III) ions at 440 nm. ESI-MS and Job’s method were used to confirm the 1:1 molar binding ratio of the receptor PEBD to Fe(III) ions. Using the Benesi-Hildebrand equation the binding constant value was determined as 8.485×103 M-1. Furthermore, the limit of detection (LOD, 3σ/K) value was found to be 1.81µM in DMSO/water (95/5, v/v) media. According to the Environmental Protection Agency (EPA) of the United States, it is lower than the acceptable value of Fe3+ in drinking water (0.3 mg/L). The presence of 14 other metal ions such Co2+, Cr3+, Cu2+, Fe2+, Hg2+, Pb2+, K+, Ni2+, Mg2+, Cd2+, Ca2+, Mn2+, Al3+, and Zn2+ did not interfere with the detection of Fe(III) ions. Computational studies of the receptor PEBD were carried out with density functional theory (DFT) using B3LYP/ 6-311G (d, p), LANL2DZ level of theory. Finally, molecular docking studies have been performed to investigate the Cytochrome P450 1A1(CYP1A1) protein inhibitory action of the receptor PEBD.