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    Synthesis, characterization and VOCs adsorption kinetics of diethylstilbestrol-substituted metallophthalocyanines
    (World Sci Publ Co Inc, 2019) Kaki, Esra; Gogsu, Nurcan; Altindal, Ahmet; Salih, Bekir; Bekaroğlu, Özer
    Compound (4,4'-hex-3-ene-3,4-diyl)bis(4,1-phenylene)bis(oxy)diphthalonitrile 3 was synthesized by the reaction of 4-nitrophthalonitrile 1 and diethylstilbestrol 2 in dry DMF in presence of dry K2CO3 . New mononuclear phthalocyanines 4-6 were obtained from compound 3 by addition of the corresponding metal salts [Co(OAc)(2)center dot 4H(2)O, Zn(OAc)(2)center dot 2H(2)O and Cu(OAc)(2)]. The novel compounds were characterized by elemental analysis and FT-IR, UV-vis, H-1-NMR and MALDI-TOF mass spectroscopy techniques. The effects of four main groups of organic vapors on these novel compounds were studied and discussed. The adsorption kinetics of alkanes (n-hexane and n-octane), alcohols (methanol and 2-proponal), chlorinated hydrocarbons (dichlommethane and trichloromethane) and amines (diethylamine and triethylamine) on 4-6 were examined using three adsorption kinetic models: the Elovich equation, the pseudo-first-order equations and Ritchie's equation. Results show that the linear regression analysis with respect to the pseudo-second-order rate equations generates a straight line that best fits the data of adsorption of alcohols and chlorinated hydrocarbons on Pc films. On the other hand, the Elovich equation generates a straight line that best fits the data of adsorption of alkanes and amines.
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    Synthesis, characterization and VOCs adsorption kinetics of diethylstilbestrol-substituted metallophthalocyanines
    (World Scientific Publishing Co., 2020) Kaki, Esra; Göğsu, Nurcan; Altındal, Ahmet; Salih, Bekir; Bekaroğlu, Özer
    Compound (4, 4'-hex-3-ene-3, 4-diyl)bis(4, 1-phenylene)bis(oxy)diphthalonitrile 3 was synthesized by the reaction of 4-nitrophthalonitrile 1 and diethylstilbestrol 2 in dry DMF in presence of dry K2CO3. New mononuclear phthalocyanines 4-6 were obtained from compound 3 by addition of the corresponding metal salts [Co(OAc)2. 4H2O, Zn(OAc)2. 2H2O and Cu(OAc)2]. The novel compounds were characterized by elemental analysis and FT-IR, UV-vis, 1H-NMR and MALDI-TOF mass spectroscopy techniques. The effects of four main groups of organic vapors on these novel compounds were studied and discussed. The adsorption kinetics of alkanes (n-hexane and n-octane), alcohols (methanol and 2-proponal), chlorinated hydrocarbons (dichloromethane and trichloromethane) and amines (diethylamine and triethylamine) on 4-6 were examined using three adsorption kinetic models: the Elovich equation, the pseudo-first-order equations and Ritchie’s equation. Results show that the linear regression analysis with respect to the pseudo-second-order rate equations generates a straight line that best fits the data of adsorption of alcohols and chlorinated hydrocarbons on Pc films. On the other hand, the Elovich equation generates a straight line that best fits the data of adsorption of alkanes and amines.
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    Synthesis, characterization, and DFT study of novel metallo phtalocyanines with four carboranyl clusters as photosensitisers for the photodynamic therapy of breast cancer cells
    (Elsevier, 2019) Sener, Sevil; Bayrac, A. Tahir; Sener, B. Bilgenur; Tozlu, Cem; Acar, Nursel; Salih, Bekir; Yuksel, Mithat; Bekaroğlu, Özer
    The synthesis and characterization of novel Zn(II) and Co(II) phthalocyanines 4 and 5, respectively containing four o-carboranyl units (40 boron atoms, 32.5% boron by weight) at the peripheral positions are described. The phthalocyanines (Pcs) were synthesized by cyclotetramerization of the previously prepared precursor 4-(2-thiol-o-carboranyl)thiolato-phthalonitrile 3 with the presence of metal salt in boiling dry DMF under a dry nitrogen atmosphere. They were characterized by elemental analysis, UV-Vis, FT-IR, MALDI-TOF mass and H-1 NMR spectrometry. To elucidate the structural, spectroscopic and bonding properties of the obtained compounds, calculations with DFT/TD-DFT(Density Functional Theory/Time Dependent-Density Functional Theory) were performed. The cytotoxic effects of 4 and 5 on cancer cells and epithelial cells were determined. The targeted cytotoxicities of both compounds against cancer cells were analyzed with the cell viability test. Although, 4 caused less PDT (Photodynamic therapy) based decrease in cell viability of cancer cell line in comparison to 5, it showed comparatively high cytotoxicity against cancer cells but not epithelial cells. The IC50 (half maximal inhibitory concentration) values indicate that 4 with PDT shows 17.3 fold more cytotoxicity to breast cancer cells than epithelial cells. The selectivity in cytotoxicity of 4 makes it a good candidate for cancer treatment. Interestingly, 5 was found to be highly cytotoxic for both cancer and epithelial cell lines. Considerably, 5 might be used as a cancer drug when combined with targeting agents such as antibodies and aptamers.
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    Synthesis, characterization, DFT study, conductivity and effects of humidity on CO2 sensing properties of the novel tetrakis- [2-(dibenzylamino)ethoxyl] substituted metallophthalocyanines
    (Elsevier Science Sa, 2020) Senoglu, Sema; Ozer, Metin; Dumludag, Fatih; Acar, Nursel; Salih, Bekir; Bekaroğlu, Özer
    Novel tetrakis[2-(dibenzylamino)ethoxyll substituted nickel (II), cobalt (II) and manganese (II) phthalocyanines were synthesized by using 4-(2-(dibenzylamino)ethoxy)phthalonitrile with corresponding metal salts in 2-N, N-dimethylaminoethanol. New phthalonitrile ligand was prepared from 2-(dibenzylamino)ethan-l-ol and 4-nitrophthalonitrile in acetonitrile at reflux temperature using potassium carbonate as catalyst. The compounds was characterized by elemental analysis, infrared, ultraviolet-visible and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopic methods. Density functional theory calculations were performed for structural and electronic properties. Direct current and alternating current conductivity properties of the metallophthalocyanine films were investigated between 293 - 523 K and frequencies 40 -100 kHz. The direct current conductivity values were calculated as 5.29 x 10(-10 )S/cm, 2.39 x 10(-9)S/cm, and 3.04 x 10(-10) S/cm, for nickel, cobalt and manganese complexes (293 K) films, respectively. Activation energies of the films were 0.50-0.70 eV for T < 478 K. Alternating current conductivity results suggest that hopping model explains dominant charge transport mechanisms. Carbon dioxide sensing properties (1000-8000 ppm) of the metallophthalocyanine films were investigated at room temperature (293 K) in air as background. Additionally, effects of the relative humidity on carbon dioxide sensing properties were also investigated for relative humidity between 0-80 % RH in air. Response and response time values of the films were reported. Newly synthesized phthalocyanine complexes in this study were found to be reversible and sensitive to the carbon dioxide gas in humid air. Carbon dioxide sensing measurements revealed that sensitivity of the sensors increased with increasing carbon dioxide concentration and relative humidity. It is found that manganese phthalocyanine showed greater sensitivity than nickel- and cobalt phthalocyanine complexes.
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    Synthesis, characterization, in vitro cytotoxicity of novel metallo phthalocyanines with four methylpropiophenonyl clusters and their effects on caenorhabditis elegans thermotolerance
    (SPRINGER INT PUBL AG, 2022) Şenoğlu, Sema; Güleç, Meltem; Yavuz Dokgöz, Elif; Bal Öztürk, Ayça; İzbudak, Burçin; Salih, Bekir; Olgun, Abdullah; Ceyhan, Tanju
    Phthalocyanines (Pcs) have the potential to be used in many medical applications. Novel Zn (II), Co (II), and Cu (II) phthalocyanines (Pcs) 4, 5, and 6, respectively, containing four methylpropiophenonyl units at the peripheral positions were described. Pcs were synthesized by cyclotetramerization of the previously prepared precursor 2-hydroxy-4'-[2-(3,4-dicyanophenoxyethoxy)]-2-methylpropiophenone 3 with the presence of metal salts under nitrogen atmosphere. The compounds were characterized by elemental analysis, IR (Infrared spectroscopy), UV-visible spectroscopy, and Laser Desorption ionization time-of-flight mass spectroscopy (LDI-TOF-MS) methods. The compounds were tested for in vitro cytotoxicity in cultured human cells, and thermotolerance in Caenorhabditis elegans (C. elegans). Standard MTT assays were carried out for cytotoxicity testing using HeLa and L929 cells. Results showed that there was no significant decrease in the cell viability with zinc (II), cobalt (II), and copper (II) phthalocyanines (ZnPc, CoPc, and CuPc) at 0.25 mu M concentration. C. elegans survival assay with ZnPc, CoPc, and CuPc under heat stress showed that although a dose-dependent statistically significant toxicity was observed for ZnPc and CuPc, CoPc was not toxic at all concentrations tested and even increased the survival of worms at the 0.050-0.250 mu M concentration range. Therefore, CoPc can be a lead compound for further preclinical studies for its potential in photodynamic therapy (PDT) and anti-aging purposes.
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    Synthesis, characterization, OFET, and DFT study of the novel ball-type metallophthalocyanines bridged with four diaminopyrimidine-dithiol
    (World Sci Publ Co Inc, 2020) Molla, Fadime; Yazici, Aysegul; Salcuki, Nursel Acar; Altindal, Ahmet; Salih, Bekir; Bekaroğlu, Özer
    Co2Pc2 (2) and Zn2Pc2 (3) were obtained in DMF and LuPc2 (4) was obtained in hexanol by the cyclotetramerization of novel diphthalonitrile (1). Synthesized compounds were characterized by FT-IR, H-1-NMR, elemental analyses, MALDI-TOF MS and UV-vis spectroscopy techniques. Optimized geometries and electronic structures for compounds 2, 3 and 4 were investigated by Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TD-DFT). In compound 2, a new bond was observed between Co centers forming two Co(III) with the interaction of d orbitals. Computational and experimental UV-vis spectra in DMF were found in agreement for the investigated compounds. Vertical and adiabatic ionization potentials for the studied systems were also calculated. The gate dielectric performances of thin films obtained from these compounds were investigated by fabricating ITO/2-4/Au devices. The observed reverse bias J-V characteristics revealed that the leakage current in ITO/2-4/Au devices is because of the Poole-Frenkel effect. The effect of the gate dielectric on the OFET performance parameters was also investigated by fabricating bottom-gate top-contact OFET using pentacene as the active layer. Maximum field effect mobility was observed with the 2-based OFET device. Calculated HOMO-LUMO gap, hole reorganization energy and ionization energy have also supported the experimental results which indicate that 2 is the most suitable system for OFET devices.
  • Küçük Resim Yok
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    Synthesis, characterization, OFET, and DFT study of the novel ball-type metallophthalocyanines bridged with four diaminopyrimidine-dithiol
    (World Scientific Publishing Co. Pte. Ltd., 2022) Molla, Fadime; Yazici, Aysegul; Selcuki, Nursel Acar; Altindal, Ahmet; Salih, Bekir; Bekaroğlu, Özer; Ball-Type Phthalocyanines; Density Functional Theory
    Co2Pc2 (2) and Zn2Pc2 (3) were obtained in DMF and LuPc2 (4) was obtained in hexanol by the cyclotetramerization of novel diphthalonitrile (1). Synthesized compounds were characterized by FT-IR, 1H-NMR, elemental analyses, MALDI-TOF MS and UV-vis spectroscopy techniques. Optimized geometries and electronic structures for compounds 2, 3 and 4 were investigated by Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TD-DFT). In compound 2, a new bond was observed between Co centers forming two Co(III) with the interaction of d orbitals. Computational and experimental UV-vis spectra in DMF were found in agreement for the investigated compounds. Vertical and adiabatic ionization potentials for the studied systems were also calculated. The gate dielectric performances of thin films obtained from these compounds were investigated by fabricating ITO/2-4/Au devices. The observed reverse bias J-V characteristics revealed that the leakage current in ITO/2-4/Au devices is because of the Poole-Frenkel effect. The effect of the gate dielectric on the OFET performance parameters was also investigated by fabricating bottom-gate top-contact OFET using pentacene as the active layer. Maximum field effect mobility was observed with the 2-based OFET device. Calculated HOMO-LUMO gap, hole reorganization energy and ionization energy have also supported the experimental results which indicate that 2 is the most suitable system for OFET devices
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    Synthesis, conductivity, and ımpedance studies on metallophthalocyanines formed across adjacent rings
    (Wiley-V C H Verlag Gmbh, 2019) Sener, Sevil; Selcuki, Nursel Acar; Dumludag, Fatih; Salih, Bekir; Bekaroğlu, Özer
    The synthesis and characterization of Co-II, Zn-II, and Ni-II phthalocyanines (Pcs) 4, 5, and 6, respectively, containing two bis[2-(4-hydroxyphenyl)-2-propyl]benzene groups formed across adjacent rings at the peripheral positions are described. The Pcs were synthesized by cyclotetramerization of the previously prepared precursor 4,4 '-bis[1,3-propylbenzene-2-p-phenoxy]phthalonitrile (3) in the presence of metal salt in boiling dry DMF under a dry nitrogen atmosphere. Elemental analysis, UV-Vis, FT-IR, and H-1-NMR spectroscopy, as well as MALDI-TOF mass spectrometry techniques were used for the characterization of 4. Conductivity (dc and ac) and impedance spectroscopy (IS) measurements were performed on the films of 5 and 6 between the temperatures 293 and 523 K and frequencies 40 and100 kHz. The dc conductivity values were calculated as 2.11 x 10-(10), 3.48 x 10-(10), and 1.90 x 10-(10) S/cm for the films of 4, 5, and 6, respectively, at room temperature. Activation energy values of the films were also calculated. Conductivity (ac) results suggest that the dominant charge transport mechanisms can be explained by the hopping model depending on temperature and frequency range. From impedance spectra and Cole-Cole plots, the relaxation time in the Debye dispersion relation is considered as a distribution of relaxation time values rather than as a single relaxation time. To elucidate the structural, spectroscopic, and bonding properties of the obtained compounds, DFT/TD-DFT calculations were performed.