Thiochalcone substituted phthalocyanines for dye-sensitized solar cells: Relation of optical and electrochemical properties for cell performance

Karaca, Hüseyın; Şişman, İlkay; Güzel, Emre; Sezer, Serdar; Selimoğlu, Faysal; Ergezen, Bahar; Karaca, Meryem; Eyüpoğlu, Volkan

doi:10.1080/00958972.2018.1468027

Cited by 18 publications

(6 citation statements)

References 66 publications

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“…MPcs showed an irrevesible oxidation at 0.70, 0.79 V and a reversible reduction peaks−1.12, −1.24 V for ZnPC and CoPc respectively, which can be assigned to ring based‐redox processes. [ 80 ] An additional oxidation peak was appeared in CV of CoPc at 0.46 as cobalt is redox active matal which results from the fact that central atom 3d orbitals of MPcs lie between HOMO and LUMO orbitals of the system at CoPcs but below the HOMO level of the system at ZnPcs. [ 81,82 ] CoPcs display blue shifted Q band maxima in the absorption spectra compared to ZnPc because the complexes bearing open‐shell metal ions like cobalt (II) interact strongly with the Pc compared to zinc (II).…”

Section: Resultsmentioning

confidence: 99%

Some characteristics of new and innovative COX inhibitor derivatives: Potent hCA‐I and hCA‐II inhibitors supported by molecular docking studies

Karakılıç

Alım

Emirik

et al. 2021

Applied Organom Chemis

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In this study, two novel metallophthalocyanines (ZnPc and CoPc) were synthesized using the corresponding metal salts 4‐(4‐(4‐[4‐chlorophenyl]‐5‐methylisoxazol‐3‐yl)phenoxy)‐phthalonitrile (11), prepared from the reaction of 4‐nitrophthalonitrile and 4‐(4‐[4‐chlorophenyl]‐5‐methylisoxazol‐3‐yl)phenol (9). These metallophthalocyanines (MPcs) showed quite solubility in organic solvents such as dichloromethane (DCM), tetrahydrofuran (THF), dimethyl formamide (DMF), and dimethylsulfoxide (DMSO). The novel compounds 11a and 11b have been characterized using their UV–Vis, FT–IR, 1H NMR, 13C NMR, X‐Ray, and MALDI–TOF mass spectra. Supporting information cocerning with the study has been supplied. Photochemical, photophysical, and cyclic voltagram properties of these novel 4‐(4‐(4‐[4‐chlorophenyl]‐5‐methylisoxazol‐3‐yl)phenoxy substituted metallophthalocyanines (11a and 11b) were determined in DMF. DNA binding, metal chelating effect assay, and DPPH [2,2‐diphenyl‐1‐picrylhydrazyl hydrate] radical scavenging assay and electrochemical studies of MPcs were investigated. Further, the inhibitory effects of the COX‐inhibitor based novel metallophthalocyanines (11a and 11b) and their ligands (10 and 11) were examined on human erythrocyte carbonic anhydrase I (hCA‐I) and II (hCA‐II) isoenzymes, and the synthesized molecules exhibited very strong inhibitory effects on both isoforms. In addition, the hCA‐I and hCA‐II inhibition potential of Zn (II) and Co (II) Phthalocyanine complexes was supported by molecular docking studies. The binding interaction of metallophthalocyanines complexes 11a, 11b enzymes were analyzed in detail.

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Section: Resultsmentioning

confidence: 99%

Some characteristics of new and innovative COX inhibitor derivatives: Potent hCA‐I and hCA‐II inhibitors supported by molecular docking studies

Karakılıç

Alım

Emirik

et al. 2021

Applied Organom Chemis

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“…These central metal ions are important in regulating the properties of MPcs. [6] Pcs are of great interest due to the diversity of their interesting optical, electronic and structural properties and serve as active compounds in different fields, especially in materials science and medicine; some of these are liquid crystals, [7] nonlinear optical applications, [8] organic solar cells, [9][10][11] catalyst, [12][13][14] chemical sensors [15] and photodynamic therapy. [16][17][18] Recently, researchers have also studied the antioxidant and antimicrobial activities of Pc molecules.…”

Section: Introductionmentioning

confidence: 99%

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

et al. 2023

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This study describes the synthesis and characterization of peripherally and non‐peripherally substituted copper(II) and cobalt(II) phthalocyanines bearing tetraethyleneglycol monomethyl ether chains. In addition, the metal‐free and zinc(II) phthalocyanine derivatives were prepared according to the referred procedure. All newly synthesized phthalocyanines were characterized using some spectroscopic techniques such as elemental analysis and fourier transform infrared, ultraviolet‐visible, and mass spectroscopies. The effects of solvent type and concentration on aggregation properties of phthalocyanines were studied, as well. The biological activities of a series of these peripherally and non‐peripherally tetra‐substituted phthalocyanines were investigated. The effects of the central metal ion and the position of the substituent on biological activities of phthalocyanines were also compared. When the antioxidant activities of the synthesized molecules were evaluated by the 2,2‐diphenyl‐1‐picrylhydrazyl method, 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatocobalt(II) (63.17±0.012 %) showed the highest activity. The highest reducing power activity was obtained with the 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) molecule. In the antibacterial activity studies using the disc diffusion method, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy) ethoxy)ethoxy)ethoxy]phthalocyaninatocopper(II) exhibited the highest inhibition activity on both gram negative (18±0.23 mm) and gram positive (23±0.07 mm) strains. On the other hand, 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy) ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11,15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatozinc(II) compounds presented hemolytic activity against sheep blood in the hemolytic activity studies. The results confirmed that the synthesized molecules demonstrated average antioxidant activity compared to standard antioxidants. 2,9/10,16/17,23/24‐Tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy)ethoxy]phthalo‐cyaninatocopper(II), 2,9/10,16/17,23/24‐tetrakis[2‐(2‐(2‐(2‐methoxy ethoxy)ethoxy)ethoxy)ethoxy]phthalocyaninatozinc(II) and 1,8/11, 15/18,22/25‐tetrakis[2‐(2‐(2‐(2‐methoxyethoxy)ethoxy)ethoxy) ethoxy]phthalocyaninatozinc(II) complexes could remarkably inhibit S. aureus and CuPc‐1 complex E. coli growth.

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“…Their skeleton structure and functional groups also make them well-known intermediates for the synthesis of various heterocyclic and bioactive compounds [23]. In literature showed that the introduction of chalcone groups into the peripheral/nonperipheral positions of phthalocyanines increased the electrochemical properties of phthalocyanines [24][25][26][27][28]. Also, phthalocyanines bearing chalcone groups have efficient photocatalytic, photophysical and photochemical properties [29,30].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and electrochemical properties of copper(II), manganese(III) phthalocyanines bearing chalcone groups at peripheral or nonperipheral positions

2020

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In this study, new chalcone compound 1, new phthalonitrile derivatives 2 and 3, new copper(II), manganese(III) phthalocyanines bearing chalcone groups at peripheral or nonperipheral positions were synthesized. Electrochemistry of tetra-(4-{(2E)-3-[2-fluoro-4-(trifluoromethyl)phenyl]prop-2-enoyl}phenoxy) substituted Co(II)Pc and Mn(III)Pcs were studied with cyclic voltammetry (CV) to determine the redox properties of the phthalocyanines. According to the results, while the CuPcs 2a and 3a showed two Pc based reduction reactions and one Pc based oxidation reaction, MnPcs 2b and 3b gave two metalbased reduction reactions. All the redox processes are shifted toward positive potentials as a result of the increased electron-withdrawing ability of the trifluoromethyl substituents.

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Thiochalcone substituted phthalocyanines for dye-sensitized solar cells: Relation of optical and electrochemical properties for cell performance

Cited by 18 publications

References 66 publications

Some characteristics of new and innovative COX inhibitor derivatives: Potent hCA‐I and hCA‐II inhibitors supported by molecular docking studies

Some characteristics of new and innovative COX inhibitor derivatives: Potent hCA‐I and hCA‐II inhibitors supported by molecular docking studies

Investigation of Biological Activities of Tetra‐substituted Phthalocyanines Bearing Tetraethyleneglycol Monomethyl Ether Chains at Peripheral and Non‐peripheral Positions

Synthesis and electrochemical properties of copper(II), manganese(III) phthalocyanines bearing chalcone groups at peripheral or nonperipheral positions

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