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    Metallo and metal free phthalocyanines bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents: Synthesis, characterization, aggregation behavior, electronic, antioxidant and antibacterial properties
    (ELSEVIER SCIENCE SA, 2014) Agirtas, M. Salih; Guven, M. Emin; Gumus, Selcuk; Ozdemir, Sadin; Dundar, Abdurrahman
    As starting material the phthalonitrile derivative bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile derivative in the presence of corresponding metal salts gave the new metallophthalocyanines. Metal free phthalocyanine was obtained from the reaction of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile units. The novel compounds have been characterized by using various spectroscopic data. The aggregation investigations carried out in different concentrations indicate that 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-5) M in tetrahydrofuran. The antioxidant activities of novel compounds were analyzed through radical scavenging ability of 1,1-dipheny1-2-picrylhydrazyl, chelating ability to ferrous ions and reducing power. In addition to these, the antibacterial activities of compounds were investigated. Moreover, the ground-state geometries of the complexes were optimized using B3LYP/6-31G(d,p) level of density functional theory in order to predict the three-dimensional geometries and electronic structure. (C) 2014 Elsevier B.V. All rights reserved.
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    Metallo Phthalocyanines bearing 2-Isopropyl-6-methylpyrimidin-4-yloxy Substituents: Synthesis, Characterization, Aggregation Behavior, Antioxidant and Antibacterial Activity, and Electronic Properties
    (WILEY-V C H VERLAG GMBH, 2014) Agirtas, M. Salih; Dede, Emrah; Gumus, Selcuk; Dundar, Abdurrahman; Okumus, Veysi
    A novel phthalonitrile derivative bearing 2-isopropyl-6-methylpyrimidin-4-yloxy substituents at peripheral positions was synthesized by a nucleophilic substitution reaction. Metallophthalocyanines were obtained from the reaction of the novel phthalonitrile with metal Zn, Cu, Co, and Ni salts. The characterization of the compounds was performed using elemental analysis as well as UV/Vis, FT-IR, and H-1-NMR spectroscopy. The aggregation behaviors of phthalocyanine complexes were also investigated. These metallophthalocyanines do not show any aggregation behavior between 10 (4)-10 (6) M concentration range in THF. The antioxidant activities of the synthesized compounds were evaluated using three different tests: 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, metal chelating activity, and reducing power assays. All the compounds exhibited various antioxidant activities. In addition, antimicrobial activity of the compounds was tested over four gram positive and two gram negative bacteria. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D arrangements and electronic structure.