Browsing by Author "Yildiko, Umit"

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Computational Dft Calculations, Photovoltaic Properties and Synthesis of (2r, 3s)-2, 3, 4-Trihydroxybutoxy Substituted Phthalocyanines
(Taylor & Francis inc, 2020) Cabir, Beyza; Yildiko, Umit; Agirtas, Mehmet Salih; Horoz, Sabit
In this study, 4-((2R, 3S)-2, 3, 4-trihydroxybutoxy) phthalonitrile was synthesized and characterized as starting material. This new starting material reacts with cobalt and copper metal salts to obtain metallophthalocyanine complexes. The electronic absorption of cobalt and copper phthalocyanine compounds in different concentrations of THF was investigated. In addition, the solubility and absorption of the compounds in different solvents were investigated. Density functional theory was also performed to support the relevant experimental results of the synthesized copper and cobalt center atomic compound. The photovoltaic performance of compounds was measured as current density-voltage (J-V).
Design of Novel Substituted Phthalocyanines; Synthesis and Fluorescence, Dft, Photovoltaic Properties
(Tubitak Scientific & Technological Research Council Turkey, 2020) Agirtas, Mehmet Salih; Solgun, Derya Gungordu; Yildiko, Umit; Ozkartal, Abdullah
The 4-(2[3,4-dimethoxyphenoxy] phenoxy) phthalonitrile was synthesized as the starting material of new syntheses. Zinc, copper, and cobalt phthalocyanines were achieved by reaction of starting compound with Zn(CH3 COO)(2), CuCl2, and CoCl2 metal salts. Basic spectroscopic methods such as nuclear magnetic resonance electronic absorption, mass and infrared spectrometry were used in the structural characterization of the compounds. Absorption, excitation, and emission measurements of the fluorescence zinc phthalocyanine compound were also investigated in THE. Then, structural, energy, and electronic properties for synthesized metallophthalocyanines were determined by quantum chemical calculations, including the DFT method. The bandgap of HOMO and LUMO was determined to be chemically active. Global reactivity (I, A, eta, s, mu, chi, omega) and nonlinear properties were studied. In addition, molecular electrostatic potential (MEP) maps were drawn to identify potential reactive regions of metallophthalocyanine (M-Pc) compounds. Photovoltaic performances of phthalocyanine compounds for dye sensitive solar cells were investigated. The solar conversion efficiency of DSSC based on copper, zinc, and cobalt phthalocyanine compounds was 1.69%, 1.35%, and 1.54%, respectively. The compounds have good solubility and show nonlinear optical properties. Zinc phthalocyanine gave fluorescence emission.
Dft Analysis and Electronic Properties, and Synthesis of Tetra (9-Phenyl Oxy Peripheral-Substituted Zinc Phthalocyanine
(Springer int Publ Ag, 2020) Solgun, Derya Gungordu; Keskin, Mehmet Salih; Yildiko, Umit; Agirtas, Mehmet Salih
The 4-((9-phenyl-9H-xanthene-9-yl) oxy) phthalonitrile compound was synthesized and characterized as starting material. Zinc phthalocyanine was obtained by reaction of 4-((9-phenyl-9H-xanthen-9-yl) oxy) phthalonitrile with Zn(CH3COO)(2). Novel compounds were characterized using mass spectra, UV-Vis spectroscopy, H-1-NMR, C-13 NMR, and infrared spectroscopy. The fluorescence, emission, excitation, and absorption spectra of the zinc phthalocyanine compound were studied in tetrahydrofuran (THF). The determination of these properties is very useful for photodynamic therapy applications. Also, zinc phthalocyanine (Zn-Pc) was optimized with the basic set of 6-311G and LanL2DZ of the Density functional theory (DFT). The energy band-gap HOMO-LUMO of the molecule was determined. Chemical indices were calculated using HOMO-LUMO energies. The electrophilic region and the nucleophilic region were defined from the molecular electrostatic potential (MESP) maps. Dipole moment components have been calculated and can be considered as potential candidates for the design of non-linear optical materials.
Nano-ölçekli Olarak 4,5-diklorftalik Asit Metal Komplekslerinin Hazırlanması ve Elektronik Özellikler
(2020) Keskin, Mehmet Salih; Agırtas, Mehmet Salıh; Yildiko, Umit; Solğun, Derya Güngördü
Burada asit fonksiyonlu ftalik asit metal kompleksleri sentezlendi. Yapı analizi için Fourie dönüşümü kızılötesi spektroskopisi (FT-IR), X-ışını kırınım analizi (XRD), Taramalı elektron mikroskopisi-Enerji Dağıtıcı Spektrometresi (SEM + EDS) cihazları kullanılmıştır. 4,5-diklorftalik asidin bakır ve çinko komplekslerinin yapısal parametreleri, B3LYP yönteminin LanL2DZ baz seti ile belirlenmiştir. HOMO (en yüksek işgal edilen moleküler orbital) ve LUMO (en düşük işgal edilmeyen moleküler orbital) enerjileri ve elektron yoğunluk dağılım potansiyeli (MEP) gibi elektronik özellikler elde edildi. Hiperkonjugatif etkileşimlerden kaynaklanan moleküllerin stabilitesi, yük delokalizasyonu, doğal bağ orbital (NBO) analizi kullanılarak analiz edildi. Zn ve Cu-4,5-diklorftalik asidin (DCPA) teorik ve deneysel FT-IR spektrumlarının karşılaştırılması yapıldı ve Cu için R = 0.97204 ve Zn kompleksi için R = 0.97929 doğrusal çalışmalar formunda bulundu. İki karakterizasyon sonucunun tutarlı olduğu bulunmuştur.
Photovoltaic Performance Properties, Dft Studies, and Synthesis of (e)-3 Acrylic Acid Substituted Phthalocyanine Complexes
(Springer int Publ Ag, 2021) Solgun, Derya Gungordu; Yildiko, Umit; Ozkartal, Abdullah; Agirtas, Mehmet Salih
In this study, firstly, a new phthalonitrile derivative was synthesized from the reaction of caffeic acid with phthalonitrile. Then, metal phthalocyanine complexes were obtained from the reaction of this phthalonitrile derivative with metal salts. Compounds were characterized by UV, NMR, IR and Mass spectroscopy methods. In addition, the fluorescence and electronic properties of the diamagnetic zinc phthalocyanine compound were investigated. The performances of dye-sensitized solar cells of compounds were examined. The calculated power conversion efficiencies (eta %) of the complexes using the obtained current density (J)-voltage (V) curves were determined that these compounds can be used as promising sensitizers in solar cell applications. The calculated power conversion efficiencies (% eta) of the complexes were found to be at a reasonable level. Molecular orbital properties such as HOMO-LUMO energy gap, Fermi Energies, state density spectrum, and molecular electrostatic potential surfaces were calculated for each phthalocyanine molecule. In addition, the amount of phthalocyanine required for ideal dye sensitivity was investigated.
Synthesis of Axial Bis(benzo[d][1,3]dioxol-5 Silicon (Iv): Photophysical and Photochemical Properties and Docking Studies on Dna-Sipc Interactions
(Wiley-v C H verlag Gmbh, 2022) Solgun, Derya Gungordu; Yildiko, Umit; Agirtas, Mehmet Salih
The synthesis of an axial phthalocyanine compound by the reaction of piperonyl alcohol and SiPcCl2 has been reported. Its structure was characterized by compound (HNMR)-H-1,(CNMR)-C-13, Mass, FTIR and UV visible spectroscopy. Photophysical and photochemical properties of the compound were investigated by fluorescence spectroscopy. The photosensitizer performance of the compound was determined. In addition, with the quantum chemical study, the HOMO - LUMO band gap and the optimized structure of the compound were investigated with two basic sets of the TD-DFT B3LYP method. The band gap (Delta E) was found to be in the range of 0.6-0.7 eV, and it was determined that the compound would require low energy in the chemotherapeutic interaction with light and in its stimulation. As a chemotherapy drug candidate, its adhesion to protein and DNA structure has been evaluated as in-silico. In this context, the potential binding and interaction aspects of the new chemotherapeutically effective phthalocyanine compound with two kinds of homo sapiens protein-DNA complexes were investigated by molecular docking approach. It bonded with the phthalocyanine compound in both crystal structures. A docking score of 6.315 kcal/mol was obtained in the 6DIA encoded DNA polymerase beta substrate complex.
Synthesis of Axially Silicon Phthalocyanine Substituted With Bis- (3,4-Dimethoxyphenethoxy) Groups, Dft and Molecular Docking Studies
(Springer, 2022) Solgun, Derya Gungordu; Tanriverdi, Aslihan Aycan; Yildiko, Umit; Agirtas, Mehmet Salih
Axially bis-substituted silicon phthalocyanine was synthesized from the reaction of 2-(3,4-dimethoxy phenyl) ethanol and SiPcCl2. The structure of the compound was justified by FT-IR, (1) H NMR, (13) C NMR, UV-Vis, and mass spectra. The conglomeration action of the phthalocyanine compound was determined by UV-visible spectra at different concentrations and in different solvents. Some parameters of this axial silicon phthalocyanine compound were investigated by computational chemistry. Structural optimization of axial silicon phthalocyanine substituted with compound, HOMO-LUMO energies and MEP maps was performed by density functional theory (DFT) studies. In addition, a chemical bond analysis of the molecule was performed with quantum theory atom in molecules (QTAIM). Finally, a molecular docking study was applied to this new phthalocyanine molecule in its binding mechanism. [GRAPHICS] .
Synthesis of Bis-(benzhydryloxy) Substituted Axially Silicon(Iv) Phthalocyanine: Investigation of Photophysical, Photochemical, and Computational Electronic Properties
(Taylor & Francis Ltd, 2024) Solgun, Derya Gungordu; Yildiko, Umit; Agirtas, Mehmet Salih
Synthesis of axially disubstituted silicon(IV) phthalocyanine bearing benzhydryloxy groups obtained by reaction of SiPcCl2 with diphenylmethanol is reported. Characterization of the compound was performed by H-1 and C-13 NMR, UV-Vis, mass spectrometry, and FT-IR spectroscopy. Photophysical and photochemical properties were investigated. Fluorescence spectra measurements were performed in DMSO as solvent. A preferred chemical method was used to determine the amount of singlet oxygen production. Optimizations were calculated for the single-molecule Si-Pc with the 6-311 G (d, p) basis set at the B3LYP and B3PW91 levels of density functional theory (DFT). The charge transfer (or) charge delocalization between intramolecular donor-acceptor groups was determined by NBO analysis. Furthermore, molecular electrostatic potential, Fukui functions, electrophilic and nucleophilic character maps were calculated. The electronic structure and energy parameters of the investigated compound were determined to be Delta E-calc = 2.19 eV by DFT calculation and Delta E-opt = 1.84 by experimental UV spectrum.
Synthesis, Antioxidant, Dna Cleavage and Antimicrobial Properties of Phthalocyanine Complexes Bearing the Poly-Hydroxyl Groups
(Springer int Publ Ag, 2021) Agirtas, Mehmet Salih; Cabir, Beyza; Yildiko, Umit; Ozdemir, Sadin; Gonca, Serpil
(4-((1-((2-(bis(2-hydroxypropyl) amino) ethyl) (2-hydroxypropyl) amino) propan-2-yl) oxy) phthalonitrile) (BHHP) was synthesized from reaction N, N, N ', N '- tetrakis (2-hydroxypropyl) ethylene diamine (SM) with 4-nitro phthalonitrile. Zinc, cobalt and copper phthalocyanine complexes were achieved from the reaction of BHHP compound with metal salts. Quantum chemical studies of these phthalocyanines have been computationally supported using density functional theory methods. The antioxidant properties of phthalocyanine compounds were determined with the help of l, l-diphenyl-2-picrilhydrazyl radical scavenging ability and chelating ability to iron ions. Compound 6 showed 72.8% inhibition of DPPH free radicals at 200 mg/L concentration and compound 4 showed 71.5% ferrous metal chelating activity at 200 mg/L concentration. The antimicrobial and DNA cleavage activities of compounds were also investigated. All tested phthalocyanine compounds showed excellent nuclease activity at all concentration. Antimicrobial activities of phthalocyanine compounds were detected using broth microdilution method and all test compounds demonstrated perfect antimicrobial activities. According to in vitro studies, copper phthalocyanine compound 6 has the best activity against the P. aeruginosa with 8 mu g/mL of MIC value.
Synthesis, Dft Analysis, and Electronic Properties of New Phthalocyanines Bearing Etaeo Substituents on Peripheral Position
(Taylor & Francis Ltd, 2019) Cabir, Beyza; Yildiko, Umit; Agirtas, Mehmet Salih
This study reports the synthesis of new zinc and magnesium phthalocyanine compounds with ((ethylenediamine-N,N ',N '-triacetic acid-N-2-ethyl)oxy) (ETAEO) substituted groups. A novel compound, (4-ETAEO) phthalonitrile, for the starting material of these phthalocyanines was synthesized. The exact characterization of the compounds was carried out with H-1 NMR, IR, UV-Vis, and mass spectra. Fluorescence intensity of these metallophthalocyanines (MPcs) was investigated at 1 x 10(-5) M concentration in tetrahydrofuran (THF). Electronic absorption measurements of the phthalocyanine compounds in the tetrahydrofuran were performed. Photodegradation was performed in dimethylformamide (DMF). Optimized structure, boundary molecular orbitals (HOMO and LUMO), natural bond orbital (NBO) analysis and global reactivity descriptors were analyzed by DFT calculations.
Synthesis, Dft Calculations, Photophysical, Photochemical Properties of Peripherally Metallophthalocyanines Bearing (2-(benzo[d] [1,3] Dioxol-5 Phenoxy) Substituents
(Taylor & Francis Ltd, 2022) Solgun, Derya Gungordu; Yildiko, Umit; Agirtas, Mehmet Salih
4-(2-(benzo[d] [1,3] dioxol-5-ylmethoxy) phenoxy) phthalonitrile was first prepared as a starting material. Then, this new phthalonitrile derivative was reacted with Zn and Co salts to obtain new phthalocyanine complexes. Phthalocyanine complexes were evaluated by fluorescence emission, extinction, and absorption measurements. Aggregation studies show compliance with the lambert-beer law in the concentration range studied for peripheral phthalocyanine compounds. The density functional theory calculations of the metallophthalocyanines compounds were performed using the B3LYP method- LanL2DZ basis set to derive structural optimization, HOMO-LUMO energy parameters, and nonlinear Optical properties. The calculated values of metallophthalocyanines with different center atoms were obtained close to each other. Molecular electronic surface maps of the studied compounds are mapped and discussed. The HOMO-LUMO energy gaps of our compounds studied are around 2.1 eV. The docking studies were performed with the phthalonitrile.
Synthesis, Photophysical, Photochemical, and Dft Properties of a Zinc Phthalocyanine With 2-(2 Peripheral Groups
(Taylor & Francis Ltd, 2022) Solgun, Derya Gungordu; Yildiko, Umit; Agirtas, Mehmet Salih
The 2-nitrophenol and 4-nitrophthalonitrile reagents were mixed in the presence of potassium carbonate in dimethylformamide (DMF) under N-2 at room temperature. Then, by adding thymol(5-methyl-2-isopropylphenol) and continuing the reaction, 4-(2-(2-isopropyl-5-methylphenoxy)phenoxy)phthalonitrile was obtained. Zinc phthalocyanine (4) was formed from the reaction of ZnCl2 and 4-(2-(2-isopropyl-5-methylphenoxy)phenoxy)phthalonitrile (3) at 190 degrees C. Both compounds were soluble in most organic solvents. Compounds 3 and 4 were characterized by mass, infrared, electronic absorption and nuclear magnetic resonance spectroscopies. The concentration-absorption relationship of 4 was examined by UV spectroscopy. The photophysical and photochemical properties of 4 were investigated. The geometry-optimized structures of 4 were investigated with the DFT approach, B3PW91/6-31G (d,p), and B3LYP/LanL2DZ basis set. Energy properties, first order hyperpolarizability, and Fukui function calculations were also performed. Natural bond orbital analysis was performed to explain the charge transfer (or) charge delocalization due to intramolecular interactions in phthalocyanine.
Synthesis, Theoretical Dft Analysis, Photophysical and Photochemical Properties of a New Zinc Phthalocyanine Compound
(Taylor & Francis inc, 2024) Agirtas, Mehmet Salih; Solgun, Derya Gungordu; Yildiko, Umit
In this study, fluorescent zinc phthalocyanine compound was synthesized using 4-(2-(4-(2-phenylpropan-2-yl) phenoxy) phenoxy) phthalonitrile and zinc metal salt. The structure of compounds was characterized by using H-1, and C-13 NMR, FT-IR, Mass, UV-Vis spectroscopy. The fluorescence emission, excitation and absorption properties of this phthalocyanine compound were studied in tetrahydrofuran and DMSO. Aggregation behaviors for different concentrations in the same solvent were investigated. Quantum chemical calculations were performed using 6-311G basis set of DFT (B3LYP and CAMB3LYP) methods. The structural optimization, molecular orbital analysis, and electronic properties of the synthesized phthalocyanine were then determined in the ground state and gas phase of the DFT method. Moreover, molecular electrostatic potential (MEP) maps were drawn to identify the reactive regions of the zinc phthalocyanine complex. The data of the study show that the phthalocyanine complex can be used as sensor agent for biological fluorescence analysis.