Electrochemical, spectroelectrochemical characterization and electropolymerization of 2-(4-methyl-1,3-thiazol-5-yl)ethoxy-substituted manganese and indium phthalocyanines

Yenilmez, H. Yasemin; Akdağ, Özgün; Sevim, Altuğ Mert; Koca, Atıf; Bayır, Zehra Altuntaş

doi:10.1016/j.poly.2015.08.012

Cited by 13 publications

(5 citation statements)

References 34 publications

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“…Hence, hybridization of the thiazole ring and diverse biochemically active groups can result in materials exhibiting wonderful medical properties (8–10). Recently, photophysical, electrochemical and spectroelectrochemical properties of phthalocyanines bearing thiazole groups have been studied (11–17). Phthalocyanine (Pc) and its derivatives consist of a planar 18π‐electron system that results in high electron transfers that in turn lead to excellent electronic, optical, chemical and physical properties (18–20).…”

Section: Introductionmentioning

confidence: 99%

Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

Farajzadeh

Özdemir

Gonca

et al. 2021

Photochem & Photobiology

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As thiazoles and fluorinated groups are well known as active species of hybrid pharmaceutical agents, this study aimed to evaluate the synergic effect of these groups on the biological features of phthalocyanines for the first time in the hope of discovering efficient pharmaceutical agents. Therefore, a new phthalonitrile derivative namely 4‐(2‐(4‐methylthiazol‐5‐yl)ethoxy)‐5‐(4‐(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal‐free (2)/metal phthalocyanines (3‐5) were prepared and characterized using various spectroscopic techniques. Solubility of new phthalocyanines (2‐5) was examined in a series of polar and nonpolar solvents. Additionally, sono/photochemical methods were applied to examine the photophysical and sono/photochemical properties of new zinc phthalocyanine to measure its potential as a probable material for sono/photodynamic therapies. The antioxidant activities of compounds (1‐5) were evaluated using the DPPH scavenging activity method and the highest radical scavenging activity was obtained 92.13% (200 mg L−1) for manganese phthalocyanine. All the phthalocyanines demonstrated high DNA nuclease activity, as well. The antimicrobial activities of compounds (1‐5) were investigated using disk diffusion and microdilution methods. The phthalocyanines exhibited effective microbial cell inhibition activity against Escherichia coli (E. coli). Antimicrobial photodynamic therapy activity was investigated against E. coli by LED irradiation. Compounds (2‐5) acted as photosynthesizers. Also, they displayed significant biofilm inhibition activity against Staphylococcus aureus (S. aureus) and Pseudomonas aeruginosa (P. aeruginosa).

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Section: Introductionmentioning

confidence: 99%

Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

Farajzadeh

Özdemir

Gonca

et al. 2021

Photochem & Photobiology

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“…We prepared, in this study, new phthalocyanines carrying four 4-(4-methoxyphenyl)-2-thiazole-2-thio moieties and studied their electropolymerization properties in detail. The MPcs prepared were subjected to cyclic voltammetry and square wave voltammetry to study their electrochemical and spectroelectrochemical behaviors as to how the molecules respond to the electrochemical applications [36][37][38][39]. Table 1 lists the basic parameters, which include halfpeak potential (E 1/2 ), anodic-cathodic peak potential separation (ΔE p ), anodic-cathodic peak current ratio (I pa /I pc ) and the difference between the first oxidation and the first reduction potentials (ΔE 1/2 ) used in the CV and SWV scans.…”

Section: Voltammetric and Spectroelectrochemical Measurementsmentioning

confidence: 99%

Synthesis, electrochemistry, and electrocatalytic activity of thiazole-substituted phthalocyanine complexes

Demir

Yenilmez

Koca

et al. 2022

J Solid State Electrochem

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We report the synthesis of non-peripheral metallophthalocyanines which carry four 4-(4-methoxyphenyl)-2-thiazole-2-thio units. 1 H-NMR, FT-IR, UV-Vis, and MS data were acquired to characterize the synthesized compounds. Voltammetric and in situ spectroelectrochemical measurements shed light on the redox properties of the metallophthalocyanines (MPcs) in order to show the influence of the metal cations and thiazole-bearing substituents. In solution, the redox processes had an influence to the electrochromic responses, which were examined with in situ spectrocolorimetry. Phthalocyanines having cobalt (II), manganese (III), iron (III), and zinc (II) at the center yielded characteristic redox couples which are metal-and/ or Pc-based and which are harmonious with the common redox properties of these types of compounds. In situ spectroelectrochemistry provided the information that MPc species underwent distinct color changes during electron transfer reactions. Electropolymerization of all complexes was performed on glassy carbon electrode, and the electropolymerized film of FePc was evaluated as an active electrocatalyst, in the alkaline medium, for oxygen evolution reaction (OER).

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“…Redox properties of Pcs determine the applicability in the electrochemical technological areas [29] . Modifications of Pcs with functional groups expand the redox richness and flexibility in different electrochemical applications [30] . Many alternatives for the Pc compounds can be designed by using various central metals and substituents (peripheral, nonperipheral, axial, tetra, or octa substitution), to enrich the redox properties [31] .…”

Section: Introductionmentioning

confidence: 99%

Electrochemical and in-situ spectroelectrochemical properties of novel (5-(tert-butyl)-2-((3,4-dicyanophenoxy)methyl)phenyl)methanolate substituted mononuclear metal phthalocyanines

Şahin

Akdağ

Orman

et al. 2023

Journal of Molecular Structure

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Electrochemical, spectroelectrochemical characterization and electropolymerization of 2-(4-methyl-1,3-thiazol-5-yl)ethoxy-substituted manganese and indium phthalocyanines

Cited by 13 publications

References 34 publications

Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

Synthesis, electrochemistry, and electrocatalytic activity of thiazole-substituted phthalocyanine complexes

Electrochemical and in-situ spectroelectrochemical properties of novel (5-(tert-butyl)-2-((3,4-dicyanophenoxy)methyl)phenyl)methanolate substituted mononuclear metal phthalocyanines

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