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YALÇIN, BAHATTİN

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2019 - 201912020 - 20233
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Author: SALAN, ÜMİT × Subject: Phthalocyanine ×

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Now showing 1 - 4 of 4
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    Novel lutetium(III) phthalocyanine-coumarin dyads; synthesis, characterization, photochemical, theoretical and antioxidant properties
    (ELSEVIER SCIENCE SA, 2021) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Koksoy, Baybars; Yalcin, Bahattin; Taskin, Turgut; Selcuki, Nursel Acar; Salan, Umit; Durmus, Mahmut; Bulut, Mustafa
    In this study, novel 7-oxy-3-ethyl-6-hexyl-4-methylcoumarin substituted lutetium(III) phthalocyanine compounds were synthesized, characterized and their photochemical, theoretical, and antioxidant properties were examined. All complexes were characterized by common spectroscopic methods such as FT-IR, UV?vis, 1H NMR, MALDI-TOF-MS and elemental analysis as well. Geometry optimization of phthalocyanine compounds was calculated in the B3LYP functional using 6-31G (d, p) + SDD basis set of the Density Functional Theory. Aggregation, singlet oxygen generation, and photodegradation behavior under light irradiation of the complexes (1?4) were investigated in dimethylformamide. The three phthalocyanine compounds (1, 2, and 4) showed a high level of singlet oxygen efficiency were compared with the unsubstituted zinc(II) and lutetium(III) phthalocyanine compounds because their quantum yield values were found to be over 0.80. The radical cation scavenging activities of the compounds 3 (120.344 mM trolox/mg) and 4 (188.733 mM trolox/mg) are quite remarkable in 2,2?-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid analysis according to butylated hydroxyanisole (52.63 mM trolox/mg).
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    1,2,3-Triazole incorporated coumarin carrying metal-free, Zn(II), Mg(II) phthalocyanines: Synthesis, characterization, theoretical studies, photophysical and photochemical properties
    (ELSEVIER SCIENCE SA, 2020) YALÇIN, BAHATTİN; Ozdemir, Mucahit; Abliatipova, Aziza; Benian, Sueda; Yalcin, Bahattin; Salan, Umit; Durmus, Mahmut; Bulut, Mustafa
    In this study, the preparation of two novel phthalonitrile compounds, 7-(propargyloxy)-3-(3,4-dicyanophenoxyphenyl)coumarin (1), and 7-(propargyloxy)-3-(2,3-dicyanophenoxy-phenyl)coumarin (2) were performed. Two new coumarinyl-1,2,3-triazole hybrids, (1-phenethy1-1H41,2,A-triazole 4 yl) 7 methyleneoxy 3 [F. (3,4 dicya nophenoxy)phenyl]-coumarin (3), and (1-phenethy1-1H-[1,2,3]-triazole 4 yl) 7 methyleneoxy 3 [F. (2,3 dicya nophenoxy)phenyl]-coumarin (4), were synthesized by the copper(I)-catalysed Huisgen 1,3-dipolar cycloaddition reaction of 2-(azidoethyl)benzene with terminal ethynyl bearing coumarin derivatives (1 or 2). These novel phthalonitrile derivatives (3 and 4) were converted into their peripheral (5-7) and non-peripheral (8-10) metal-free, zinc(II) and magnesium(II) phthalocyanine counterparts. The synthesized phthalocyanine derivatives are first examples on the phthalocyanine-coumarin derivatives bearing triazole ring. The structures of all these novel compounds were characterized by variety of spectroscopic techniques including FT-IR, UV-vis, H-1 NMR, MALDI-TOF MS and elemental analysis. The photophysicochemical properties of all studied Pcs (5-10) were determined in dimethyl sulfoxide. The zinc(II) and magnesium(II) phthalocyanines bearing triazole containing coumarin substituents appear to be useful as Type II photosensitizers because the singlet oxygen quantum yields ranged in acceptable values from 0.17 to 0.49 confirmed that these phthalocyanines can be suggested as photosensitizers in Photodynamic Therapy applications. Geometry optimization, frequency analysis and molecular orbital energy values of coumarin/triazole substituted phthalocyanine were performed in Density Functional Theory method using the B3LYP/LANL2DZ level of theory.
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    Photophysical and photochemical properties and comparison of tolyl and tosyl coumarin-bearing phthalocyanines
    (2023-02-15) ÖZDEMİR, MÜCAHİT; YALÇIN, BAHATTİN; SALAN, ÜMİT; Kazancıçok Z., Güler H. E., ÖZDEMİR M., PİŞKİN M., Bulut M., YALÇIN B., SALAN Ü.
    © 2022In this study, peripheral and non-peripherally substituted Zn(II) phthalocyanine complexes were synthesized from 7‑hydroxy-3-(p-tolyl)coumarin and 7‑hydroxy-3-(p-tosyl)coumarin compounds. The synthesized new compounds were characterized using elemental analysis, FT-IR, UV–Vis, Fluorescence 1HNMR spectroscopy and MALDI-TOF mass spectrometry. All the synthesized phthalocyanine complexes showed good solubility in organic solvents such as acetone, dichloromethane, chloroform, pyridine, and ethyl acetate. Fluorescent quenching behavior was investigated using 1,4-benzoquinone and potassium iodide as a quencher. The photophysical (fluorescent quantum yields and lifetimes) and photochemical (single oxygen and photodegradation quantum yields) properties of these new phthalocyanines were examined in dimethyl sulfoxide. Phthalocyanine complexes containing 7‑hydroxy-3-(p-tolyl)coumarin had higher singlet oxygen quantum yields than phthalocyanine complexes containing 7‑hydroxy-3-(p-tosyl)coumarin. Phthalocyanines to which coumarins are peripherally bound were more advantageous than their non-peripherally bound derivatives. As a result of their photophysical and photochemical properties, coumarin-phthalocyanine complexes containing tolyl-/tosyl- groups can be used as photosensitizing candidates in photodynamic therapy and can be developed with targeted modifications.
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    7-Oxy-3,4-cyclohexenecoumarin Carrying Novel Zinc(II) and Indium(III) Acetate Phthalocyanines: Synthesis, Characterization, Photophysical and Photochemical Properties
    (WILEY-V C H VERLAG GMBH, 2019) YALÇIN, BAHATTİN; Karapinar, Beguemhan; Oezdemir, Muecahit; Salan, Uemit; Durmus, Mahmut; Yalcin, Bahattin; Bulut, Mustafa
    In this study, 7-hydroxy-3,4-cyclohexenecoumarin (1), two new phthalonitriles, 7-(2,3-dicyanophenoxy)-3,4-cyclohexene-coumarin (2), 7-(3,4-dicyanophenoxy)-3,4-cyclohexenecoumarin (3), were prepared. The phthalonitrile derivatives 2 and 3 were converted to the respective non-peripheral tetra, peripheral tetra 7-oxy-3,4-cyclohexenecoumarin substituted zinc(II) (4,6) and indium(III)acetate phthalocyanine (5,7) derivatives. All novel purified compounds (2-7) were characterized by elemental analysis, FT-IR, UV-vis, (HNMR)-H-1, 13CNMR, MALDI-TOF mass data. The spectral, photophysical (fluorescence quantum yields and lifetimes), and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of the synthesized Pcs (4-7) were studied in DMF, and the results were compared to determine the effects of the locations of substituents and the diversity of the central metal atom on these properties. The 7-oxy-3,4-cyclohexenecoumarin bearing phthalocyaninatozinc(II) and indium(III)acetate complexes showed good solubility in organic solvents such as chloroform, dichloromethane, tetrahydrofuran, acetone, DMF and DMSO. The fluorescence quenching behavior were investigated using 1,4-benzoquinone as a quencher. They have an acceptable level of singlet oxygen production, which determines the usability of phthalocyanines in photodynamic therapy applications and demonstrated appropriate photodegradation. The thermal properties of Pcs (4-7) were also investigated.