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    7-Oxy-3-(3,4,5-trimethoxyphenyl)coumarin substituted phthalonitrile derivatives as fluorescent sensors for detection of Fe3+ ions: Experimental and theoretical study
    (Elsevier Science Sa, 2014) Kaya, Esra Nur; Yuksel, Fatma; Ozpinar, Gul Altinbas; Bulut, Mustafa; Durmus, Mahmut
    The novel 7-hydroxy-3-(3,4,5-trimethoxyphenyl) coumarin (1) has been synthesized via Perkin reaction and its phthalonitrile derivatives (2, 3, 4 and 5) have also been prepared from the reaction of this coumarin (1) with 3-nitrophthalonitrile, 4-nitrophthalonitrile or 4,5-dichlorophthalonitrile compounds for the first time in this study. The newly synthesized compounds have been fully characterized by H-1 NMR, MALDI-TOF, FT-IR, UV-vis and fluorescence spectral data as well as elemental analysis. The exact structure of the coumarin substituted phthalonitrile derivatives (2, 3 and 5) have also been determined using X-ray diffraction. The electronic absorption and fluorescence properties of these new compounds have been studied in different solvents. The chemosensor behaviors of these compounds to metal ions have also been examined by fluorescence spectroscopy and these compounds exhibited as fluorescence chemosensor for the determination of Fe3+ ions in solution. Fe3+ complex structures of mono-coumarin ring substituted derivatives (1-4) have been investigated by using density functional theory computations. (C) 2013 Elsevier B.V. All rights reserved.
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    New metallophthalocyanines including benzylphenoxy groups and investigation of their organic-field effect transistor (OFET) features
    (Elsevier Sci Ltd, 2022) Ozdemir, Mucahit; Altinisik, Sinem; Koksoy, Baybars; Canimkurbey, Betul; Koyuncu, Sermet; Durmus, Mahmut; Bulut, Mustafa
    In this study, metal and metal-free novel phthalocyanines containing peripheral and non-peripheral tetra 2-ben-zylphenoxy groups were synthesized. The compounds were characterized by UV-Vis, FT-IR, H-1 NMR, and MALDI-TOF mass spectrometry as well as elemental analysis. These new phthalocyanines exhibited excellent solubility in most organic solvents, and their redox behavior was investigated in different solvents such as dimethyl sulfoxide (DMSO) and dichloromethane (DCM). The redox behavior of the peripheral and non-peripheral phthalocyanine compounds 1a -c and 2a -c was determined by cyclic voltammetry and in situ spec-troelectrochemistry. According to organic field-effect transistors (OFETs) measurements, the peripheral and non-peripheral phthalocyanine-cobalt complexes which have higher mobility than others were utilized top-gate bottom-contact OFETs fabrication. The output characteristics of the device show that its mobility is approximately 5 x 10(-2) cm(2)/Vs with p-type accumulation.
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    Photophysical and photochemical properties and comparison of tolyl and tosyl coumarin-bearing phthalocyanines
    (Elsevier, 2023) Kazancicok, Zehra; Guler, Hatice Esar; Ozdemir, Mucahit; Piskin, Mehmet; Bulut, Mustafa; Yalcin, Bahattin; Salan, Umit
    In this study, peripheral and non-peripherally substituted Zn(II) phthalocyanine complexes were synthe-sized from 7-hydroxy-3-(p-tolyl)coumarin and 7-hydroxy-3-(p-tosyl)coumarin compounds. The synthe-sized new compounds were characterized using elemental analysis, FT-IR, UV-Vis, Fluorescence 1 HNMR 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 io-dide 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 prop-erties, coumarin-phthalocyanine complexes containing tolyl-/tosyl-groups can be used as photosensitiz-ing candidates in photodynamic therapy and can be developed with targeted modifications.(c) 2022 Elsevier B.V. All rights reserved.
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    Spectroscopic, photophysical and photochemical properties of newly metallo-phthalocyanines containing coumarin derivative
    (Elsevier, 2020) Capkin, Aylin; Piskin, Mehmet; Durmus, Mahmut; Bulut, Mustafa
    The new, well-soluble and non-aggregated peripheral or non-peripheral tetra-ethyl 7-oxy-4,8-dimethylcoumarin-3-propanoate substituted magnesium (II), zinc (II) and indium (III) acetate phthalocyanines were synthesized. They were characterized by widely known spectroscopic methods such as UV-vis, IR, MALDI-TOF Mass, H-1 NMR spectroscopies and elemental analysis. Photophysical and photochemical properties were studied in N, N-dimethylformamide to determine the usability of each of these phthalocyanines as photosensitizers. The influences of the position and presence of the coumarin derivative at the phthalocyanine skeleton and metal' nature in the phthalocyanine cavity on photophysical and photochemical properties were investigated by comparing with previous analogues (magnesium, zinc, and indium phthalocyanines containing coumarin derivative with different functional groups). The spectroscopic, photophysical, photochemical data and results obtained for each of these phthalocyanines show that they may have the potential to be used as photosensitizers in photodynamic therapy. (c) 2020 Elsevier B.V. All rights reserved.