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    The microwave-assisted synthesis and structural characterization of novel, dithia-bridged polymeric phthalocyanines containing a substituted thiophenylamine Schiff base
    (Elsevier Sci Ltd, 2009) Degirmencioglu, Ismail; Bayrak, Riza; Er, Mustafa; Serbest, Kerim
    Novel polymeric metal-free and metallo(Cu(II), Co(II), Ni(II), Zn(II) and Pb(II))-phthalocyanine complexes were synthesized using microwave irradiation and the products were purified by several (crystallization and preparative thin layer) techniques. The newly prepared compounds were characterized by a combination of elemental analyses, IR, H-1/C-13 NMR,H-1-H-1 COSY, MS and UV-Vis spectroscopy. In order to better understand the spectroscopy data (especially for H-1/C-13 NMR and H-1-H-1 COSY techniques), computational calculations were used for characterization at DFT/6-31G(d) level. The electronic spectra exhibited an intense pi -> pi* transition with characteristic Q and B bands of the phthalocyanine core. (C) 2009 Elsevier Ltd. All rights reserved.
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    New olefinic centred binuclear clamshell type phthalocyanines: Design, synthesis, structural characterisation, the stability and the change in the electron cloud at olefine-based symmetrical diphthalonitrile fragment by the combined application of UV-Vis electronic structure and theoretical methods
    (Pergamon-Elsevier Science Ltd, 2011) Degirmencioglu, Ismail; Bayrak, Riza; Er, Mustafa; Serbest, Kerim
    The olefinic centred Schiff base (3) was obtained from the condensation of substituted dialdehyde (1) with 2-amino-4-methylphenol (2) in a 1:2 ratio. The diphthalonitrile derivative (5) was prepared by the reaction of 4-nitrophthalonitrile (4) and compound (3) in dry dimethylformamide/potassium carbonate. The key product (5) was obtained by nucleophilic substitution of an activated nitro group into an aromatic ring. The cyclotetramerization of compound (5) with phthalonitrile (6) in 1:6.15 ratio gave the expected metal-free phthalocyanine of clamshell type (7), and with metal salts of Zn(II), Ni(II), Co(II) and Cu(II) gave metallophthalocyanines of clamshell types (8-11), respectively in dimethylaminoethano1/1,8-diazabycyclo[5.4.0]undec-7-ene system. The products were purified by several techniques such as crystallization and preparative thin layer chromatography. The newly prepared compounds were characterised by a combination of elemental analyses, IR, H-1/C-13 NMR, MS and UV-Vis spectroscopy. (C) 2011 Elsevier Ltd. All rights reserved.
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    Novel phthalocyanines containing substituted salicyclic hydrazone-1,3-thiazole moieties: Microwave-assisted synthesis, spectroscopic characterization, X-ray structure and thermal characterization
    (Elsevier Sci Ltd, 2010) Degirmencioglu, Ismail; Atalay, Esra; Er, Mustafa; Koysal, Yavuz; Isik, Samil; Serbest, Kerim
    Novel, metal-free and metallo(Cu, Co, Ni, Zn, Pb and Mn)phthalocyanine compounds were synthesized by exposure to microwave irradiation and the products purified. The newly prepared compounds were characterized using elemental analyses, IR, H-1/C-13 NMR, H-1-H-1 COSY measurements, MS, UV-vis spectroscopy and DTA/TG analysis. The electronic spectra exhibited an intense pi -> pi* transition with characteristic Q and B bands of the phthalocyanine core, as expected. All decomposition products obtained from DTA/TG analysis were identified: it was found that the thermal stability of each phthalocyanine compound followed the order: MnPc < Metal-free < ZnPc < PbPc < CuPc < CoPc < NiPc. (C) 2009 Elsevier Ltd. All rights reserved.
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    Spectroscopic and theoretical study of 1,2,4-triazole-3-one based salicylaldimine complexes and evaluation of superoxide-scavenging properties
    (Elsevier, 2009) Serbest, Kerim; Ozen, Arzu; Unver, Yasemin; Er, Mustafa; Degirmencioglu, Ismail; Sancak, Kemal
    Five mononuclear metal complexes of Fe(III), Co(II), Ni(II), Cu(II) and Zn(II) have been synthesized with a triazole-based Schiff base ligand, 4-{[(1E)-(2-hydroxyphenyl)methylene]amino}-5-(2-thienyl-methyl)2,4-dihydro-3H-1,2,4-triazol-3-one. The structure of the compounds have been proposed by elemental analyses, spectroscopic data i.e. IR, H-1 and C-13 NMR, UV-vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. The molecular structure and vibrational frequencies of the compounds in the ground state has been calculated by density functional using Becke's three-parameter hybrid method with the Lee, Yang and Parr correlation functional methods with the Standard B3LYP/6-31G*(d,p) basis set. The computational frequencies are in good agreement with the experimental results. The superoxide dismutase (SOD) mimetic activity of the complexes have been investigated by utilizing xanthine-xanthine oxidase assay. The results indicate that the Co(II) complex is the most potent SOD mimetic of all synthesized complexes. (C) 2009 Elsevier B.V. All rights reserved.
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    Synthesis, characterization and properties of tetra((1-hydroxyimino-methylnaphthalen-2-yloxy)methyl)ethene and its homo-dinuclear metal complexes: A combined experimental and theoretical investigation
    (Pergamon-Elsevier Science Ltd, 2010) Serbest, Kerim; Karaoglu, Kaan; Erman, Murat; Er, Mustafa; Degirmencioglu, Ismail
    Tetra((1-hydroxyiminomethylnaphthalen-2-yloxy)methyl)ethene (THIMNYOME), H4L, was synthesized by the agents of 2-hydroxy-1-naphtaldehyde, tetra(bromomethyl)ethene and hydroxylamine hydrochloride in two steps. Characterization of THIMNYOME and its dinuclear complexes was made by elemental analyses. IR, H-1- and C-13 NMR, UV-vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. In the light of these results, it was suggested that the ligand coordinate to each metal atom by the two ether oxygen, two nitrogen atoms of oxime imine (C=N) and an axial oxygen of perchlorate to form pseudo square-pyramidal complexes with Ni(II), Cu(II) and Zn(II). Molar conductivity measurements reveal that all the complexes are non-electrolytes. In addition, the full geometric optimization of the tetraoxime ligand (4) has been made by the B3LYP/6-31G(d) level in order to establish a stable conformation. Additionally, all the complex structures have been studied in the B3LYP/LANL2DZ level. NBO charge distribution and the characteristics of frontier molecular orbitals of these complexes have also been investigated in order to see the electrons movement between ligand and metal atom in the same level. (C) 2010 Elsevier B.V. All rights reserved.
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    Two novel rnacroacyclic schiff bases containing bis-N2O2 donor set and their binuclear complexes: synthesis, spectroscopic and magnetic properties
    (Elsevier Science Bv, 2009) Karaoglu, Kaan; Baran, Talat; Serbest, Kerim; Er, Mustafa; Degirmencioglu, Ismail
    Herein, we report two novel macroacyclic Schiff bases derived from tetranaphthaldehyde derivative compound and their binuclear Mn(II), Ni(II), Cu(II) and Zn(II) complexes. The structures of the compounds have been proposed by elemental analyses, spectroscopic data i.e. IR, H-1 and C-13 NMR, UV-Vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. The stoichiometries of the complexes derived from mass and elemental analysis correspond to the general formula [M2L(ClO4)(n)](ClO4)(4-n), (where M is Mn(II), Ni(II), Cu(II), Zn(II) and L represents the Schiff base ligands). (C) 2009 Elsevier B.V. All rights reserved.