A selective naked-eye chemosensor derived from 2-methoxybenzylamine and 2,3-dihydroxybenzaldehyde - synthesis, spectral characterization and electrochemistry of its bis-bidentates Schiff bases metal complexes

Abstract

A new colorimetric receptor HL, acting as a bidentate Schiff base ligand, has been synthesized by condensation of 2-methoxybenzylamine on 2,3-dihydroxybenzaldehyde in a methanolic solution. Interestingly, this chelating agent can selectively detect Cu, Co, Fe and Fe ions with a simple and an easy-to-make, well defined naked-eye visible color changes in two different solvents like acetonitrile and methanol. This bidentate ligand coordinates three metal ions of Co(II), Cu(II) and Fe(II) via nitrogen and oxygen atoms. The molecular structures of the synthesized compounds were elucidated by various physicochemical properties such as the elemental analysis, FT-IR, HNMR, UV-Vis and the Mass spectrometry. The resulting general formulae [M(L)·HO] (M(II)=Cu, Fe, Co) are proposed as mononuclear complexes. The solvatochromism properties of these compounds were studied with their absorption spectra using different solvents as methanol (MeOH), acetonitrile (AN), tetrahydrofuran (THF), dimethylformamid (DMF), dimethylsulfoxid (DMSO) and dichloromethane (DC). The Electrochemical behavior of copper complex was explored in DMF solutions by cyclic voltammetry (CV) with two working electrodes: glassy carbon (GC) and platinum electrode (Pt). This study reveals that copper complex shows successively two redox systems as Cu and Cu. The Fe and Co redox systems have also been studied in DMF and DMSO media.

Synthesis, DNA Binding, and Molecular Docking Studies of Dimethylaminobenzaldehyde-Based Bioactive Schiff Bases

“…e signal due to -CH�N appears in the range of 8.5-9.5 ppm for the compounds corresponding to azomethine group which confirms the formation of Schiff bases. Moreover, a peak appears in 3.01-3.13 ppm range attributed to the -CH 3 (6H) aliphatic for the compounds (1)(2)(3)(4)(5)(6)(7)(8). A signal at δ 1.80-2.20 ppm may be assigned to the protons of the (C-CH 2 -C, 8H) for the compounds 2,3, (C-CH 2 -C, 10H) for the compounds 4, 5, and (C-CH 2 -C, 2H) for the compounds 6-8.…”

“…Assay. e in vitro evaluation was carried out to provide antimicrobial capability of heterocyclic Schiff base derivatives (1)(2)(3)(4)(5)(6)(7)(8), and the experimental results are shown in Table 2 were calculated from the graph shown in Figure 7.…”

“…ey showed phototropism and thermochromism in the solid state used in optical and electrochemical sensors for the detection and enhancement of selectivity and sensitivity [3,4]. Due to their applications in biological, analytical, and medicinal field, and their role as catalysts in organic synthesis, heterocyclic Schiff bases are considered as one of the most potential groups of heterocyclic compounds [5].…”

“…In addition, in this work, we calculated some molecular docking parameters of compounds in order to correlate them with their antimicrobial activity. (1)(2)(3)(4)(5)(6)(7)(8).…”

A Phenanthroimidazole‐based Fluorescent Turn‐Off Chemosensor for the Selective Detection of Cu2+ in Aqueous Media

“…[26][27][28][29][30] It is well known that chemical probes with large Stokes shifts are advisable because when incident light and emission signal are separated enough, the self-absorption can be avoided and the detection sensitivity could be improved. [36][37][38][39][40] With these points in mind, we devised a highly conjugated sensor 1 including phenanthrene-9,-10-dione and 2,3-dihydroxybenzaldehyde moieties, which was expected to have a special fluorescent character to a specific metal ion. [36][37][38][39][40] With these points in mind, we devised a highly conjugated sensor 1 including phenanthrene-9,-10-dione and 2,3-dihydroxybenzaldehyde moieties, which was expected to have a special fluorescent character to a specific metal ion.…”