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    Esterified porphyrazine complexes: Synthesis, characterization, aggregation behavior, and theoretical study
    (Taylor & Francis Inc, 2017) Gonca, Ergun; Ozpinar, Celal
    Magnesium porphyrazine having eight 5-hydroxypentylthio groups at the peripheral positions, was synthesized from 2,3-bis(5-hydroxypentylthio) maleonitrile. By the esterification reaction of octakis(5-hydroxypentylthio) porphyrazinato] Mg(II) with 3,4,5-trimethoxybenzoic acid in dicyclohexylcarbodiimide and toluene-p-sulfonic acid, esterified MgPz appending [5-thiopentyl 2-methoxy-4,6-bis(trifluoromethyl) benzoate] substituent was obtained. Further reaction of the metal-free porphyrazine with Co(II), Cu(II), Zn(II), and Fe(II) acetates have produced the metallo-porphyrazines. By reacting FePzCl with pyridine or pyrazine, the monomeric bis-axial and the oligomeric complexes were synthesized as the novel stable complexes, respectively. Their characterizations were performed by using elemental analysis, FT-IR, H-1-NMR, C-13-NMR, mass and UV-Vis spectral data. The aggregation investigations carried out in different concentrations indicate that 3,4,5-trimethoxybenzyloxy-substituted porphyrazine compounds do not have any aggregation behavior in different concentrations. Quantum chemical computations were also done to the structural and electronic properties of target compounds.
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    Metal-free and metallo-porphyrazines with eight [5-thiopentyl 2-methoxy-4,6-bis (trifluoromethyl) benzoate] substituent
    (Taylor & Francis Inc, 2017) Gonca, Ergun
    The reaction of (5-hydroxypentylthio magnesium porphyrazine) with 2-methoxy-4,6-bis(trifluoromethyl)benzoic acid in DCCI and PTSA, esterified MgPz having [5-thiopentyl 2-methoxy-4,6-bis(trifluoromethyl)benzoate] substituent was obtained. Further reactions of the metal-free porphyrazine with M2+(Mg, Co, Cu, Zn, Fe) acetates have produced the metallo-porphyrazines. Finally, by the reaction of FePzCl with pyridine or pyrazine compounds, [FePz(py)(2)] and [FePz(pyz)](n) complexes were prepared as the novel stable complexes, respectively. The target compounds have been characterized by using different spectroscopic methods such as FT-IR, UV-Vis, mass, H-1, C-13, and F-19 NMR together with elemental analysis. The aggregation and the solubility features were indicated in various concentrations and solvents.
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    Öğe
    Metal-free, metallo-, oligomeric, and monomeric porphyrazine complexes of (3-thiopropyl anthraquinone-2-carboxylate) units
    (Taylor & Francis Ltd, 2015) Gonca, Ergun
    Metal-free and metallo-porphyrazines (M = Mg, 2H, Co, Cu, Zn, or ClFe) with eight (3-thiopropyl anthraquinone-2-carboxylate) units appending on the periphery through flexible alkylthio-bridges have been synthesized through esterification of octakis(hydroxypropylthio) porphyrazinato magnesium with anthraquinone-2-carboxylic acid in the presence of dicyclohexylcarbodiimide (DCCI) and toluene-p-sulfonic acid. The synthesized compounds were characterized by FT-IR, UV-vis, (1) H and C-13 NMR, mass spectrometry, and elemental analysis. Metal-free and several metallo-porphyrazines (M = Mg, 2H, Co, Cu, or Zn) carrying eight (3-thiopropyl anthraquinone-2-carboxylate) groups at the peripheral positions were synthesized from octakis(3-hydroxypropylthio) porphyrazinato] Mg(II). Symmetrically functionalized porphyrazines with eight ester units were soluble in common organic solvents. Chloro-octakis(3-thiopropyl anthraquinone-2-carboxylate) porphyrazinato iron(III) (FePzCl) was prepared by the reaction of metal-free porphyrazine with iron(II) acetate and further treatment with hydrochloric acid solution. The oligomeric structure [FePz(pyz)](n) and the monomeric compound [FePz(py)(2)] were formed as stable complexes by reacting FePzCl with pyrazine and pyridine, respectively. The porphyrazine compounds were characterized by different spectroscopic methods.
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    Metal-free, metallo-porphyrazines, monomeric bisaxial complex [FePz(py)2] and the bridged complex [FePz(pyz)]n with eight (4-thiobutyl 4-biphenylcarboxylate) groups
    (Taylor & Francis Ltd, 2014) Gonca, Ergun
    Metal-free and metallo-porphyrazines (M = Mg, Co, Cu, Zn, and ClFe) carrying eight hydroxybutylthio groups at peripheral positions were prepared from 2,3-bis(4-hydroxybutylthio) maleonitrile. The hydroxybutyl groups were incorporated by esterification of porphyrazine derivatives with 4-biphenylcarboxylic acid in the presence of dicyclohexylcarbodiimide and p-toluenesulfonic acid. Unlike the parent porphyrazine, the symmetrically functionalized porphyrazines with eight ester units were soluble in common organic solvents such as chloroform, dichloromethane, tetrahydrofuran, acetone, and toluene and insoluble in water and n-hexane. Chloro-octakis(4-thiobutyl 4-biphenylcarboxylate) porphyrazinato iron(III) (FePzCl) was prepared by the reaction of metal-free porphyrazine with iron(II) acetate and further treatment with HCl solution. The monomeric bisaxial complex [FePz(py)(2)] and the bridged complex [FePz(pyz)](n) were formed as stable complexes by reacting FePzCl with pyridine and pyrazine, respectively. The newly synthesized compounds were characterized by elemental analysis, FT-IR, UV-vis, mass, H-1 and C-13 NMR spectroscopy.
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    Metallo-porphyrazines with eight [5-thiopentyl 3,4,5-tris(benzyloxy)benzoate] groups: Synthesis, characterization, aggregation, and solubility behavior
    (Elsevier, 2017) Gonca, Ergun
    Metal-free and metallo-porphyrazines having eight 5-hydroxypentylthio units at the peripheral positions have been prepared from 2,3-bis(5-hydroxypentylthio)maleonitrile. By the esterification reaction of magnesium hydroxy-porphyrazine with 3,4,5-tris(benzyloxy)benzoic acid in dicyclohexylcarbodiimide and toluene-p-sulfonic acid, the reactivity of the hydroxypentyl units was indicated. On the other hand, iron porphyrazine derivatives with eight [5-thiopentyl 3,4,5-tris(benzyloxy)benzoate] groups attached to the periphery positions were synthesized. By the reaction of metal-free porphyrazine with iron (II) acetate and further processing with HCl solution, FePzCl was obtained. Finally, by reacting FePzCl with pyridine or pyrazine, [FePz(py)(2)] and [FePz(pyz)](n) complexes were prepared, respectively. The characterizations of target complexes were carried out by utilizing different spectroscopic methods such as FT-IR, UV-vis, mass, H-1 NMR, and C-13 NMR together with elemental analysis. (C) 2016 Elsevier B.V. All rights reserved.
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    New polyfluorinated porphyrazine complexes: synthesis, characterization, aggregation, and solubility
    (Taylor & Francis Ltd, 2017) Gonca, Ergun
    By cyclotetramerization of 2,3-bis(2,3,5,6-tetrafluoro-4-methylbenzylthio) maleonitrile in the presence of magnesium butoxide, magnesium porphyrazinate (MgPz) carrying eight (2,3,5,6-tetrafluoro-4-methylbenzylthio) functional units on the periphery positions has been synthesized. Conversion of MgPz into the metal-free derivative was achieved upon addition of a strong acid such as trifluoroacetic acid. Further reaction of this product with different metal(II) acetates led to metallo porphyrazines (MPz). The monomeric bisaxial complex FePz(py)(2) as well as the bridged complex [FePz(pyz)]n were formed as stable complexes by reacting FePzCl with pyridine or pyrazine, respectively. These complexes were characterized by elemental analysis, together with FT-IR, H-1 NMR, C-13 NMR, F-19 NMR, UV-vis, and mass spectral data. [GRAPHICS] .
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    Synthesis and Characterization of Octakis(4-biphenyl)-2-seco-2,3-Dioxoporphyrazinato Iron Derivatives
    (Taylor & Francis Inc, 2015) Gonca, Ergun
    Chloro-[octakis(4-biphenyl)-2-seco-2,3-dioxoporphyrazinato] iron(III) (FePzCl) was prepared by the reaction of octakis(4-biphenyl)-2-seco-porphyrazine-2,3-dione with iron(II) acetate and further treatment with HCl solution. The monomeric bisaxial complex [FePz(py)(2)] as well as the bridged complex [FePz(pyz)](n) were formed as stable complexes by reacting FePzCl with pyridine or pyrazine, respectively. These new iron porphyrazine derivatives were characterized by elemental analysis, together with FT-IR, UV-Vis, mass, H-1, and C-13 NMR spectral data.