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Öğe Metal-free, zinc(II) and lead(II) phthalocyanines functioning with 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate groups: Synthesis and investigation of photophysical and photochemical properties(Elsevier Science Sa, 2016) Demirbas, Umit; Piskin, Mehmet; Barut, Burak; Bayrak, Riza; Durmus, Mahmut; Kantekin, HalitIn this study, the synthesis and characterization of 3-(2H-benzo[d][1,2,3]triazol-2-yl)-4-hydroxyphenethyl methacrylate substituted novel phthalonitrile compound and its peripherally substituted zinc(II) lead(II) and metal-free phthalocyanine derivatives were performed for the first time. This novel compounds were characterized by obtained data from general spectroscopic methods such as FT-IR, H-1 NMR, C-13 NMR and mass. The photophysical and photochemical properties of these phthalocyanines were investigated in N,N-dimethylformamide solutions for determination of their photosensitizing abilities in photocatalytic applications such as photodynamic therapy. The lead(II) phthalocyanine complex did not produce any fluorescent in N,N-dimethylformamide because of the heavy atom effect of bigger lead atom. The fluorescence quantum yields of studied zinc(II) and metal-free phthalocyanines were found to quite higher than unsubstituted zinc(II) phthalocyanine due to substitution of the phthalocyanine skeleton. The influence of substituent and variety of the central metal ions on spectroscopic, photophysical and photochemical properties were also determined and compared. (C) 2016 Elsevier B.V. All rights reserved.Öğe The determination of photophysical and photochemical parameters of novel metal-free, zinc(II) and lead(II) phthalocyanines bearing 1,2,4-triazole groups(Elsevier Science Sa, 2016) Demirbas, Umit; Piskin, Mehmet; Bayrak, Riza; Unluer, Dilek; Dugdu, Esra; Durmus, Mahmut; Kantekin, HalitIn this study the synthesis and characterization of novel phthalonitrile compound (3) and its metal-free (4), zinc(II) (5), and lead(II) (6) phthalocyanines bearing four 4-(4-methoxyphenylethyl)-5-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one groups at peripheral positions were synthesized for the first time. These novel compounds were fully characterized by FT-FT-IR, H-1 NMR, UV-vis and MALDI-TOF mass spectroscopic techniques. Their photochemical and photophysical properties were also investigated in N, N-dimethylformamide solutions. In addition, the effect of 4(4-methoxyphenylethyl)-5-propyl-2,4dihydro-3H-1,2,4-triazol-3-one groups as substituents and central metal ions (without metal, zinc(II) or lead(II)) in the phthalocyanine cavity on these properties were also compared. The studied zinc(II) or lead (II) phthalocyanines can be potential Type II photosensitizers for photodynamic therapy in cancer applications because these phthalocyanines showed good singlet oxygen generation and appropriate photodegradation. (C) 2016 Elsevier B.V. All rights reserved.Öğe Zinc(II) and lead(II) phthalocyanines bearing thiadiazole substituents: Synthesis, characterization, photophysical and photochemical properties(Elsevier, 2019) Demirbas, Umit; Piskin, Mehmet; Bayrak, Riza; Durmus, Mahmut; Kantekin, HalitIn this study; phthalonitrile compounds 4-((5-methyl-1,3,4-thiadiazol-2-yl)thio)phthalonitrile (4) and 3-((5-methyl-1,3,4-thiadiazol-2-yl)thio)phthalonitrile (5) were synthesized. These compounds were converted to their respective peripherally and non-peripherally tetra-substituted zinc(II) (6 and 7) and lead(II) (8 and 9) phthalocyanine derivatives. The novel phthalocyanine complexes were characterized by using different spectroscopic techniques including FT-IR, UV-Vis, H-1 NMR and mass. The spectroscopic, photochemical and photophysical properties of the phthalocyanines were investigated for determination of their potential as photosensitizers for photodynamic therapy. In addition, the effects of the substituent, binding position and the variety of central metal ions in phthalocyanine core on photochemical and photophysical properties were determined. (C) 2019 Elsevier B.V. All rights reserved.