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Zekeriya Bıyıklıoğlu - One of the best experts on this subject based on the ideXlab platform.
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novel peripherally tetra substituted octacationic metal free and Metallophthalocyanines synthesis spectroscopic characterization and aggregation behaviours
Synthetic Metals, 2012Co-Authors: İrfan Acar, Zekeriya Bıyıklıoğlu, Volkan Cakir, Halit KantekinAbstract:Abstract In this study, new 1,3-bis[3-(diethylamino)phenoxy]propan-2-ol 1 and phthalonitrile derivative 3 bearing 1,3-bis[3-(diethylamino)phenoxy]propan-2-ol substituent at peripheral position have been synthesized. The synthesis, characterization of the tetra-4-(2-[3-(diethylamino)phenoxy]-1-{[3-(diethylamino)phenoxy]methyl}ethoxy) substituted metal-free 4 and Metallophthalocyanines 5, 6, 7, (MPcs, M = Ni, Co, Cu) are reported for the first time. These new metal-free and Metallophthalocyanines 4–7 were converted into water soluble quaternized products by the reaction with methyl iodide 4a–7a. The metal-free phthalocyanine 4 was prepared from phthalonitrile derivative 3 in n-pentanol with a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). Metallophthalocyanines 5–7 were prepared by cyclotetramerization of 3 with the corresponding metal salts (NiCl 2 , CoCl 2 , CuCl 2 ) in n-pentanol with a catalytic amount of DBU. The aggregation behaviours of the phthalocyanine complexes were studied in different solvents and concentrations. The new compounds have been characterized by using UV–vis, IR, 1 H NMR, 13 C NMR, MS spectroscopic data and elemental analysis.
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synthesis characterization and aggregation properties of water soluble metal free and Metallophthalocyanines peripherally tetra substituted with 2 2 dimethylamino ethoxy ethoxy moiety
Synthetic Metals, 2012Co-Authors: Zekeriya BıyıklıoğluAbstract:Abstract In this study, novel metal-free 2, cobalt 3 and copper 4 phthalocyanines were synthesized and characterized for the first time. These new phthalocyanines 2–4 were converted into water-soluble quaternized products 2a–4a by the reaction with methyl iodide. The quaternized complexes 2a–4a show excellent solubility in both organic and aqueous solutions which make them potential photosensitizer for use in PDT. Aggregation properties of metal-free and Metallophthalocyanines were investigated at different concentrations in chloroform, dimethylsulfoxide, dimethylformamide, tetrahydrofuran and water. While all synthesized metallophthalocyanine complexes did not show aggregation in chloroform, THF and DMSO, metal-free phthalocyanine showed aggregation in DMSO. The new compounds have been characterized by using UV–vis, IR, 1H-NMR, elemental analysis, MS spectroscopic data.
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Novel water-soluble metal-free and Metallophthalocyanines: Synthesis, spectroscopic characterization and aggregation properties
Synthetic Metals, 2011Co-Authors: Zekeriya BıyıklıoğluAbstract:Abstract In this study, the preparation of novel metal-free phthalocyanine 2, metallophthalocyanine complexes 3, 4, 5, 6 (MPcs, M = Ni, Co, Cu, Fe) with 6-oxyquinoline functional group and quaternized metallophthalocyanine derivatives 3a, 4a, 6a (MPcs, M = Ni, Co, Fe), was achieved. The reaction of 4-(quinolin-6-yloxy)phthalonitrile 1 in 2-(dimethylamino)ethanol as the solvent, the metal-free phthalocyanine 2 was synthesized. The synthesis of Metallophthalocyanines 3–6 derived from 4-(quinolin-6-yloxy)phthalonitrile 1 were carried out by microwave irradiation. Aggregation properties of Pcs were investigated at different concentrations in chloroform, dimethylsulfoxide, dimethylformamide and water. The metal-free phthalocyanine 2 showed the aggregation in polar solvent DMSO, whereas in chloroform no aggregation was observed. The effect of the concentration on the aggregation properties of complexes 2, 3, 4 and 5 were studied in chloroform. No aggregation was demonstrated in chloroform from concentration between 1 × 10−5 and 0.4 × 10−5 M. The new compounds have been characterized by using elemental analysis, UV–Vis, IR, 1H NMR, 13C NMR and MS spectroscopic data.
Hiroyuki Sasabe - One of the best experts on this subject based on the ideXlab platform.
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syntheses of new unsymmetrically dodecakis trifluoroethoxy substituted Metallophthalocyanines by a palladium catalyzed cross coupling reaction
Journal of Heterocyclic Chemistry, 2000Co-Authors: Minquan Tian, Tatsuo Wada, Hiroyuki SasabeAbstract:Novel unsymmetrical vanadyl and zinc dodecakis(2,2,2-trifluoroethoxy)phthalocyaninates with an iodo group were synthesized by a statistical condensation route. The palladium-catalyzed coupling reaction between such monoiodinated Metallophthalocyanines and terminal acetylenic derivatives gave various new unsymmetrically dodecakis(2,2,2-trifluoroethoxy)-substituted Metallophthalocyanines with extended exocyclic π-conjugation. Unsymmetrical zinc dodecakis(2,2,2-trifluoroethoxy)phthalocyaninate with a nitro group was also prepared for comparison. All the target phthalocyanines were separated by common col umn chromatography and characterized by elemental analysis, ir and 1H-nmr, uv-visible and fast-atombombardment mass spectroscopy.
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Syntheses of new unsymmetrically dodecakis(trifluoroethoxy)‐substituted Metallophthalocyanines by a palladium‐catalyzed cross‐coupling reaction
Journal of Heterocyclic Chemistry, 2000Co-Authors: Minquan Tian, Tatsuo Wada, Hiroyuki SasabeAbstract:Novel unsymmetrical vanadyl and zinc dodecakis(2,2,2-trifluoroethoxy)phthalocyaninates with an iodo group were synthesized by a statistical condensation route. The palladium-catalyzed coupling reaction between such monoiodinated Metallophthalocyanines and terminal acetylenic derivatives gave various new unsymmetrically dodecakis(2,2,2-trifluoroethoxy)-substituted Metallophthalocyanines with extended exocyclic π-conjugation. Unsymmetrical zinc dodecakis(2,2,2-trifluoroethoxy)phthalocyaninate with a nitro group was also prepared for comparison. All the target phthalocyanines were separated by common col umn chromatography and characterized by elemental analysis, ir and 1H-nmr, uv-visible and fast-atombombardment mass spectroscopy.
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Syntheses and nonlinear optical properties of nonaggregated Metallophthalocyanines
Journal of the Optical Society of America B, 1998Co-Authors: Minquan Tian, Suichi Yanagi, Keisuke Sasaki, Tatsuo Wada, Hiroyuki SasabeAbstract:Hexadecakis(2,2,2-trifluoroethoxy)-substituted vanadyl and zinc phthalocyanines, and hexadecakis(ethoxy)vanadylphthalocyanine, were synthesized and characterized. Their aggregation properties were studied by evaluation of the concentration dependence of absorption spectra. Hexadecakis(2,2,2-trifluoroethoxy)-substituted Metallophthalocyanines were found to be nonaggregated phthalocyanines even in the condensed state. However, nonfluorinated hexadecakis(ethoxy)vanadylphthalocyanine showed a redshift of the Q band in the solid state. The third-order nonlinear optical properties of these phthalocyanine films were studied by electroabsorption measurement in terms of molecular structure and aggregation. The aggregation effect enhances the macroscopic third-order nonlinearity of metallophthalocyanine. Among nonaggregated hexadecakis(2,2,2-trifluoroethoxy)-substituted Metallophthalocyanines, zinc phthalocyanine was found to have a larger macroscopic third-order nonlinearity than the vanadyl compound.
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Novel non-aggregated unsymmetrical Metallophthalocyanines for second-order non-linear optics
Journal of Materials Chemistry, 1997Co-Authors: Minquan Tian, Tatsuo Wada, Hiromi Kimura-suda, Hiroyuki SasabeAbstract:Novel soluble unsymmetrical Metallophthalocyanines with twelve 2,2,2-trifluoroethoxy groups as donor substituents and a mono-nitro or an exocyclic conjugated nitro group as an acceptor substituent have been synthesized and characterized. A study of the concentration dependence of UV–VIS absorption spectra showed they were non-aggregated phthalocyanines in solution and in doped polymer films. Second harmonic generation of spin-coated thin films of poly(methyl methacrylate) doped with these Metallophthalocyanines was observed after electric poling at 110 °C for 30 min at a fundamental wavelength of 1.064 µm.
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Electroabsorption of Metallophthalocyanines
Organic Metallo-Organic and Polymeric Materials for Nonlinear Optical Applications, 1994Co-Authors: Tatsuo Wada, Hiroyuki Sasabe, Shuichi Yanagi, Hiroshi Kobayashi, Jayant Kumar, Keisuke SasakiAbstract:Electroabsorption spectra have been measured on poly(methyl methacrylate) thin films doped with three kinds of Metallophthalocyanines: tetrakis (tert-butyl) metal-free and lead phthalocyanines, and hexadeca (trifluoroethoxy) metal-free phthalocyanine. The third-order nonlinear optical susceptibility, (Chi) (3 ) (-(omega) ; (omega) , O, O), was determined from the electric field-induced absorption change. The considerable differences in absorption, electroabsorption, and complex (Chi) (3 ) (-(omega) ; (omega) , O, O) spectral profiles of these Metallophthalocyanines are attributable to the difference in molecular aggregation states.
Nathan S. Lewis - One of the best experts on this subject based on the ideXlab platform.
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detection of organic vapors and nh3 g using thin film carbon black metallophthalocyanine composite chemiresistors
Sensors and Actuators B-chemical, 2008Co-Authors: Stephen Maldonado, Edgardo Garciaberrios, Marc D Woodka, Bruce S Brunschwig, Nathan S. LewisAbstract:Thin-film chemiresistive vapor sensors have been fabricated using composites of carbon black (CB) and Metallophthalocyanines. The resulting sensors exhibited large, rapid, and reversible relative differential resistance changes upon exposure to a series of test organic vapors. The individual sensor responses, and collective sensor array properties for classification of a series of test organic vapors, were comparable to those of chemiresistor arrays made from composites of conductors and insulating organic polymers. In addition to displaying resistance responses to volatile organic compounds, the CB/metallophthalocyanine composite sensors exhibited a high sensitivity towards trace levels of NH_3(g) under ambient temperature and pressure conditions. No degradation in sensor response was observed after nearly 12 h of repeated exposure to 30 parts per million of NH_3(g) in air. Chemiresistors formed from composites of CB and zinc phthalocyanines demonstrated responses that were comparable to those of commercial NH_3(g) sensors. The CB/metallophthalocyanine composites thus broaden the types of materials that can be used for this type of low-power chemiresistive gas sensing, and broaden the types of analytes that can be sensitively detected to include inorganic gases as well as organic vapors.
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Detection of organic vapors and NH3(g) using thin-film carbon black–metallophthalocyanine composite chemiresistors
Sensors and Actuators B-chemical, 2008Co-Authors: Stephen Maldonado, Edgardo García-berríos, Marc D Woodka, Bruce S Brunschwig, Nathan S. LewisAbstract:Thin-film chemiresistive vapor sensors have been fabricated using composites of carbon black (CB) and Metallophthalocyanines. The resulting sensors exhibited large, rapid, and reversible relative differential resistance changes upon exposure to a series of test organic vapors. The individual sensor responses, and collective sensor array properties for classification of a series of test organic vapors, were comparable to those of chemiresistor arrays made from composites of conductors and insulating organic polymers. In addition to displaying resistance responses to volatile organic compounds, the CB/metallophthalocyanine composite sensors exhibited a high sensitivity towards trace levels of NH_3(g) under ambient temperature and pressure conditions. No degradation in sensor response was observed after nearly 12 h of repeated exposure to 30 parts per million of NH_3(g) in air. Chemiresistors formed from composites of CB and zinc phthalocyanines demonstrated responses that were comparable to those of commercial NH_3(g) sensors. The CB/metallophthalocyanine composites thus broaden the types of materials that can be used for this type of low-power chemiresistive gas sensing, and broaden the types of analytes that can be sensitively detected to include inorganic gases as well as organic vapors.
Halit Kantekin - One of the best experts on this subject based on the ideXlab platform.
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New chalcone-substituted Metallophthalocyanines: Synthesis, characterization, and investigation of their properties:
Journal of Chemical Research, 2020Co-Authors: Ayse Aktas Kamiloglu, Hüseyin Karaca, Gonca Çelik, İrfan Acar, Halit KantekinAbstract:The synthesis of novel Metallophthalocyanines (M = Zn, Mg, and Co) derived from (E)-3-(3-bromophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one and (E)-3-(3-fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-on...
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synthesis and characterization of metallophthalocyanine with morpholine containing schiff base and determination of their antimicrobial and antioxidant activities
Journal of Organometallic Chemistry, 2019Co-Authors: Dilek Unluer, Ayse Aktas Kamiloglu, Sahin Direkel, Ersan Bektas, Halit Kantekin, Kemal SancakAbstract:Abstract In this work, novel metallophthalocyanine compounds (M = Zn, Cu, Co) bearing four 2-methoxy-4-{(Z)-[(4-morpholin-4-ylphenyl)imino]methyl}phenol at the peripheral positions were sythesized starting from the new phthalonitrile derivative (2). These new compounds (2–5) have been characterized by a combination of FT-IR, 1H NMR (for compounds 2 and 3), 13C NMR (for compound 2), UV–Vis (for compounds 3,4 and 5) and mass spectrophotometry techniques. Antioxidant activities of the Metallophthalocyanines were investigated by using DPPH free radical scavenging assay and FRAP (ferric ion reducing antioxidant power) method. The antimicrobial activity of the synthesized metallo phthalocyanine compounds (3–5) were determined against the selected different six standart bacteria isolates by microdilution broth assay with Alamar Blue Dye. Most affected bacteria from the compounds were standard E. coli and S. typhimurium (MIC 625 μg/ml). Standart Y. enterocolitica and S. aureus have been less affected by the compounds (MIC 10.000 μg/ml).
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novel peripherally tetra substituted octacationic metal free and Metallophthalocyanines synthesis spectroscopic characterization and aggregation behaviours
Synthetic Metals, 2012Co-Authors: İrfan Acar, Zekeriya Bıyıklıoğlu, Volkan Cakir, Halit KantekinAbstract:Abstract In this study, new 1,3-bis[3-(diethylamino)phenoxy]propan-2-ol 1 and phthalonitrile derivative 3 bearing 1,3-bis[3-(diethylamino)phenoxy]propan-2-ol substituent at peripheral position have been synthesized. The synthesis, characterization of the tetra-4-(2-[3-(diethylamino)phenoxy]-1-{[3-(diethylamino)phenoxy]methyl}ethoxy) substituted metal-free 4 and Metallophthalocyanines 5, 6, 7, (MPcs, M = Ni, Co, Cu) are reported for the first time. These new metal-free and Metallophthalocyanines 4–7 were converted into water soluble quaternized products by the reaction with methyl iodide 4a–7a. The metal-free phthalocyanine 4 was prepared from phthalonitrile derivative 3 in n-pentanol with a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7ene (DBU). Metallophthalocyanines 5–7 were prepared by cyclotetramerization of 3 with the corresponding metal salts (NiCl 2 , CoCl 2 , CuCl 2 ) in n-pentanol with a catalytic amount of DBU. The aggregation behaviours of the phthalocyanine complexes were studied in different solvents and concentrations. The new compounds have been characterized by using UV–vis, IR, 1 H NMR, 13 C NMR, MS spectroscopic data and elemental analysis.
Gennadii P. Shaposhnikov - One of the best experts on this subject based on the ideXlab platform.
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Peculiarities of solvation interaction of water-soluble Metallophthalocyanines with ethanol
Thermochimica Acta, 2004Co-Authors: Natalya Sh. Lebedeva, Olga V. Petrova, Anatolii I. Vyugin, Vladimir E. Maizlish, Gennadii P. ShaposhnikovAbstract:Physico-chemical characteristics of molecular complexes for water-soluble Metallophthalocyanines with alcohol were obtained by the method of thermogravimetric analysis. The change of aggregation state of Metallophthalocyanines in aqueous alkaline solutions which is due to the ethanol additions was explained taking into consideration the results of thermogravimetric analysis of Metallophthalocyanines crystallosolvates with ethanol.