Synthesis of salen-type Schiff base metal complexes, electropolymerization on graphite electrode surface and investigation of electrocatalytic effects

The new symmetrical bisimine (ONNO donor, salen type) Ni(II), Zn(II), and Fe(III) complexes were synthesized in one step from metal ions and monoimine ligand (HL: 4-amino-3-{[(2-hydroxynaphthalen-1-yl)methylidene] amino}phenyl)(phenyl)methanone). The complexes were characterized by analytical, spectral, conductance, magnetic, and thermal data. According to these analysis results, while the bisimine ligand, spontaneously forming during complexation, is attached to the metal by two nitrogen atoms and two phenolic oxygen atoms (N 2 O 2 ) in all complexes, in the Fe(III) complex, the fifth coordination is completed by the chlorine molecule. A square pyramidal geometry for [FeLCl] and a square planar geometry for [NiL], [ZnL] were proposed. The three-dimensional structure of [FeLC1] was also evaluated by single-crystal Xray diffraction, and the square pyramidal structure was clearly revealed. The molar conductivity data of the complexes confirmed their nonelectrolytic nature. Poly(imine) (PL) was obtained by the oxidative polymerization reaction of HL, and some of its properties were investigated. The electrochemical properties of the ligand and the complexes were studied by means of cyclic voltammetry. Highest and lowest occupied molecular orbital (HOMO-LUMO) energy levels and electrochemical band gaps were calculated. The thermogravimetric analysis (TGA) and differential thermal analysis (DTA) of the synthesized compounds were carried out. TGA results showed that the thermal stability of the complexes is high. The solid-state electrical conductivities of the iodine doped states of the synthesized compounds were measured by the fourpoint probe technique. PL has approximately 35 times higher electrical conductivity than the HL and complexes. Fluorescence-sensor properties of HL were also investigated and predicted that HL could be a selective fluorescence probe for Pb 2+ .

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“…An interpretable 1 H NMR graphic could not be obtained for the [ZnL], probably due to its low solubility. [ 26,27,35,37 ]…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, and investigation of some properties of the new symmetrical bisimine Ni(II), Zn(II), and Fe(III) complexes derived from the monoimine ligand

Portakal

Kaya

Demirayak

et al. 2021

Applied Organom Chemis

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“…UV-Vis spectra of synthetic unsymmetrical salen-type Fe(III) complexes are obtained in Figure 2. Upon complexation, the maximum absorption bands of obtained ligands were shifted to different wavelengths, indicating the coordination of the ligands to metal [29].…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…Complexes. Unsymmetrical salen-type Schiff base complexes were prepared from the obtained ligands and FeCl 3 .6H 2 O in 1 : 1 molecular ratio following the published procedure similarly [28][29][30]. 1.0 mmol FeCl 3 .6H 2 O dissolved in ethanol was added to an ethanol solution of 1.0 mmol ligand.…”

Section: Preparation Of Unsymmetrical Salen-type Schiff Basementioning

confidence: 99%

Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of Some Fe(III) Complexes Bearing Unsymmetrical Salen-Type Ligands Derived from 2-Hydroxynaphthaldehyde and Substituted Salicylaldehydes

Nguyen

Thi

Tuyen

2021

Journal of Chemistry

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Six Fe(III) complexes bearing unsymmetrical salen-type ligands derived from 2-hydroxynaphthaldehyde and substituted salicylaldehydes were synthesized by coordinating the unsymmetrical salen-type ligands with FeCl3.6H2O. The synthetic complexes were characterized by electrospray ionization mass spectra (ESI-MS), effective magnetic moments (μeff), and infrared (IR) and ultraviolet-visible (UV-Vis) spectra. The spectroscopic data are in good agreement with the suggested molecular formulae of the complexes. Their cyclic voltammetric studies in acetonitrile solutions showed that the Fe(III)/Fe(II) reduction processes are electrochemically irreversible. The in vitro cytotoxicity of the obtained complexes was screened on human cancer cell lines KB (a subline of Hela tumor cell line) and HepG2 (a human liver cancer cell line) and a normal human cell line HEK-293 (Human Embryonic Kidney cell line). The results showed that the synthetic Fe(III) complexes are highly cytotoxic and quite selective. The synthetic complexes bearing unsymmetrical salen-type ligands with different substituted groups in the salicyl ring indicate different cytotoxicity.

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“…Naphthalen-2(1H)-One. Tis unsymmetrical salen-type ligand was prepared by one-pot method including two-step reaction similarly according to the known procedure [18,19,21].…”

Section: Synthesis Of (Z)-1-(((2-((e)-(2-hydroxy-6-methoxybenzylidene...mentioning

confidence: 99%

Synthesis, Spectral Characterization, and Biological Activities of Some Metal Complexes Bearing an Unsymmetrical Salen-Type Ligand, (Z)-1-(((2-((E)-(2-Hydroxy-6-methoxybenzylidene)amino)phenyl)amino) methylene) Naphthalen-2(1H)-one

Nguyen

Thi

Bui

et al. 2023

Heteroatom Chemistry

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An unsymmetrical salen-type Schiff base ligand, (Z)-1-(((2-((E)-(2-hydroxy-6-methoxybenzylidene)amino)phenyl)amino)methylene)naphthalen-2(1H)-one, and its Zn(II), Cu(II), Co(II), Mn(II), and Fe(III) complexes were synthesized and characterized by mass (MS), nuclear magnetic resonance (NMR), infrared (IR), ultraviolet-visible (UV-Vis) spectra, and effective magnetic moments. The thermal analyses of the obtained ligand and metal complexes were conducted by thermogravimetric analysis (TGA). Antimicrobial activity of the unsymmetrical Schiff base ligand and its metal complexes were examined for Staphylococcus aureus as Gram-positive bacteria and Escherichia coli as Gram-negative bacteria. In vitro anticancer property of synthetic compounds was estimated against human cancer cell lines, a subline of Hela tumor cell line (KB), and a human liver cancer cell line (HepG-2) as well.

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Synthesis of salen-type Schiff base metal complexes, electropolymerization on graphite electrode surface and investigation of electrocatalytic effects

Cited by 16 publications

References 34 publications

Synthesis, characterization, and investigation of some properties of the new symmetrical bisimine Ni(II), Zn(II), and Fe(III) complexes derived from the monoimine ligand

Synthesis, characterization, and investigation of some properties of the new symmetrical bisimine Ni(II), Zn(II), and Fe(III) complexes derived from the monoimine ligand

Synthesis, Spectral Characterization, and In Vitro Cytotoxicity of Some Fe(III) Complexes Bearing Unsymmetrical Salen-Type Ligands Derived from 2-Hydroxynaphthaldehyde and Substituted Salicylaldehydes

Synthesis, Spectral Characterization, and Biological Activities of Some Metal Complexes Bearing an Unsymmetrical Salen-Type Ligand, (Z)-1-(((2-((E)-(2-Hydroxy-6-methoxybenzylidene)amino)phenyl)amino) methylene) Naphthalen-2(1H)-one

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