RESUMO
The novel TURN-OFF fluorescent sensors 4-(Benzo[1,3]dioxol-5-yloxymethyl)-7-hydroxy-chromen-2-one (4BHC) and 4-(6-Bromo-benzo[1,3]dioxol-5-yloxymethyl)-7-hydroxy-chromen-2-one (4BBHC) are designed and synthesized for the spectrofluorometric detection of the biologically important Fe3+ ions, which has sensitive and selective fluorescence quenching over other competitive metal ions. The effectiveness of the sensors and rapid response are validated through UV-Visible, and fluorescence spectral changes. These spectral changes could be due to the formation of coordination bond between ligand and metal ion. The binding stoichiometry of both sensors with Fe3+ ions is studied with the help of Job's plot, which gives a 1:2 coordination ratio; this is further confirmed through DFT, IR and NMR studies. The association constants of 4BHC and 4BBHC are calculated through Benesie-Hildebrand plots, and they are found to be 6 × 104 M-1 and 11.2 × 104 M-1 respectively. Following, LOD is calculated to define the range of sensitivity of the proposed sensors and is found to be 3.43 µM and 2.14 µM respectively. The chemical hardness parameter suggested that both sensors are soft molecules. In addition, low cytotoxicity levels of 4BHC and 4BBHC led to the demonstration of their efficacy in In-Vitro imaging of Fe3+ ions inside living cells, which ensures that these sensors are promising candidates for bioimaging.