Metallo-phthalocyanines containing thiazole moieties: Synthesis, characterization, electrochemical and spectroelectrochemical properties and sensor applications

Demir, Faruk; Yenilmez, H. Yasemin; Koca, Atıf; Bayır, Zehra Altuntaş

doi:10.1016/j.jelechem.2018.11.003

Cited by 27 publications

(20 citation statements)

References 54 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)(9)(10). Recently, photophysical, electrochemical and spectroelectrochemical properties of phthalocyanines bearing thiazole groups have been studied (11)(12)(13)(14)(15)(16)(17). Phthalocyanine (Pc) and its derivatives consist of a planar 18pelectron system that results in high electron transfers that in turn lead to excellent electronic, optical, chemical and physical properties (18)(19)(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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“…[ 74 ] Zn (II) Pcs, which have a redox inactive metal center, show only phthalocyanine‐based reduction and oxidation. [ 75 ] To examine the redox behavior of ZnPcs 4a and 6a , we performed an electrochemical study using a DMF/TBAPF 6 electrolyte system on a glassy carbon working electrode with the cyclic voltammogram technique. The cyclic voltammetry graph of the examined 4a and 6a complexes in the scanning range of 50–150 mV s −1 is shown in Figure 7a and b.…”

Section: Resultsmentioning

confidence: 99%

Physical–chemical studies of new, versatile carbazole derivatives and zinc complexes: Their synthesis, investigation of in vitro inhibitory effects on α‐glucosidase and human erythrocyte carbonic anhydrase I and II isoenzymes

Çol

Emirik

Alım

et al. 2022

Applied Organom Chemis

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In this study, two novel zinc–phthalocyanine complexes (4a and 6a), containing carbazole rings, were investigated. The first phthalocyanine 4a has been synthesized from 4‐(2‐(3‐acetyl‐9H‐carbazol‐9‐yl)ethoxy at the peripheral position. Likewise, the second phthalocyanine 6a has been synthesized from 4‐(2‐(3‐cinnamoyl‐9H‐carbazol‐9‐yl)ethoxy at the same position. The new phthalocyanines (Pcs) and their ligands are soluble in organic solvents, such as dimethylformamide, dimethyl sulfoxide, dichloromethane, ethyl acetate, and methanol/ethanol. The Zn (II) complexes were characterized by Fourier transform infrared spectroscopy, nuclear magnetic resonance (NMR) (except 13C NMR for complexes), elemental analysis, mass spectrometry, and UV–Vis spectroscopy. Also, photophysical and photochemical properties and cyclic voltammogram for the N‐substituted carbazole zinc–Pcs have been reported. The evaluation of carbazole Zn (II) complexes (4a and 6a) and ligands (3, 4, 5, and 6) for in vitro α‐glucosidase inhibitory activities was performed compared to standard drugs acarbose, and kinetic studies were also carried out to determine their inhibition modes. The inhibitory effects of these new Pcs (4a and 6a) and their ligands (3, 4, 5, and 6) on human erythrocytes carbonic anhydrase I (hCA I) and II (hCA II) isoenzymes were investigated. Moreover, in silico studies were also carried out to better investigate the interactions of N‐substituted carbazole containing zinc Pcs with the active sites of hCA I and II isoforms.

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“…For many years, phthalocyanines (Pcs) have been mainly investigated as promising candidates for application in (opto)electronics. Until recently, Pcs in a free-base form or with a central metal have been used in organic photovoltaic devices (OPVs) [ 15 , 16 , 17 ], organic light-emitting diodes (OLEDs) [ 18 , 19 ], or gas sensors [ 20 , 21 , 22 ]. Their effectiveness as photoinitiating systems [ 23 , 24 ] and photosensitizers [ 25 , 26 ] has also been reported.…”

Section: Introductionmentioning

confidence: 99%

Electrochemically Deposited Zinc (Tetraamino)phthalocyanine as a Light-activated Antimicrobial Coating Effective against S. aureus

et al. 2022

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Light-activated antimicrobial coatings are currently considered to be a promising approach for the prevention of nosocomial infections. In this work, we present a straightforward strategy for the deposition of a photoactive biocidal organic layer of zinc (tetraamino)phthalocyanine (ZnPcNH2) in an electrochemical oxidative process. The chemical structure and morphology of the resulting layer are widely characterized by microscopic and spectroscopic techniques, while its ability to photogenerate reactive oxygen species (ROS) is investigated in situ by UV–Vis spectroscopy with α-terpinene or 1,3-diphenylisobenzofuran as a chemical trap. It is shown that the ZnPcNH2 photosensitizer retained its photoactivity after immobilization, and that the reported light-activated coating exhibits promising antimicrobial properties towards Staphyloccocus aureus (S. aureus).

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Metallo-phthalocyanines containing thiazole moieties: Synthesis, characterization, electrochemical and spectroelectrochemical properties and sensor applications

Cited by 27 publications

References 54 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

Physical–chemical studies of new, versatile carbazole derivatives and zinc complexes: Their synthesis, investigation of in vitro inhibitory effects on α‐glucosidase and human erythrocyte carbonic anhydrase I and II isoenzymes

Electrochemically Deposited Zinc (Tetraamino)phthalocyanine as a Light-activated Antimicrobial Coating Effective against S. aureus

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