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    Determination of photophysical, photochemical and spectroscopic properties of novel lead(II) phthalocyanines
    (Pergamon-Elsevier Science Ltd, 2020) Piskin, Mehmet; Ozturk, Omer Faruk; Odabas, Zafer
    This study presents the synthesis and characterization of novel peripheral and non-peripheral tetra-2,6-dimethoxyphenoxy substituted lead(II) phthalocyanines. They were characterized by elemental analysis, IR, UV-vis, fluorescence, H-1 NMR, C-13 NMR and MALDI-TOF mass spectroscopic techniques, as well as thermogravimetric analysis. Their spectroscopic, photophysical and photochemical properties were studied in dimethylsulfoxide and compared with the above-mentioned properties of lead(II) phthalocyanines containing different substituents reported in the literature. Novel phthalocyanines can be good candidates as photosensitizers for photocatalytic reactions because they possess properties that are important for Type II mechanics, such as low photostability, sufficient singlet oxygen production, high solubility and non-aggregation behavior in commonly known organic solvents. (C) 2020 Elsevier Ltd. All rights reserved.
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    Do the positions of trimethyl groups on phthalocyanine photosensitizers improve their photochemical and photophysical properties?
    (Elsevier Science Sa, 2017) Cetinkaya, Mehmet; Piskin, Mehmet; Altun, Selcuk; Odabas, Zafer; Durmus, Mahmut
    The synthesis of novel highly soluble and non-aggregated metal-free and zinc(II) phthalocyanines containing four 2,3,5-trimethylphenoxy groups was achieved by starting phthalonitrile compounds. The phthalocyanines were characterized by elemental analysis, infrared, ultraviolet-visible and matrix assisted laser desorption/ionization time-of-flight mass spectroscopic techniques. Their photochemical and photophysical properties were also investigated in N,N-dimethylformamide. In addition, the influences of position of methyl groups on phenoxy unit and nature of metal in phthalocyanine cavity on photophysical and photochemical properties were investigated by comparing with previous analogues (phthalocyanines with 2,3,6-trimethylphenoxy and 2,4,6-trimethylphenoxy groups). (C) 2016 Elsevier B.V. All rights reserved.
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    First investigation on the photophysical and photochemical properties of azo-bridged phthalocyanine photosensitizers
    (Elsevier Science Bv, 2016) Sahin, Safinaz; Piskin, Mehmet; Altun, Selcuk; Durmus, Mahmut; Odabas, Zafer
    Novel azo-bridged indium(III) acetate phthalocyanine was synthesized by cyclotetramerization reaction of (E)-4-((2,5-dimethoxyphenyl)diazenyl)phthalonitrile. This phthalocyanine was fully characterized by FT-IR, H-1-NMR, UV-vis and MALDI-TOF mass spectroscopic techniques and elemental analyses as well. Additionally, the photophysical and photochemical properties of this phthalocyanine was investigated for the first time. The obtained results were compared with azo-bridged zinc(II) and metal-free phthalocyanine counterparts for determination of central metal effect on these properties. These results were also compared with unsubstituted zinc(II) and indium(III)acetate phthalocyanines for determination of substitution effect on the photophysical and photochemical properties. (C) 2016 Elsevier B.V. All rights reserved.
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    Novel 2,6-dimethoxyphenoxy alpha substituted phthalocyaninato metal complexes: Electrochemistry, In situ spectroelectrochemistry and oxygen electrocatalysis
    (Elsevier Science Sa, 2022) Orman, Efe Baturhan; Yazar, Zuhal; Piskin, Mehmet; Odabas, Zafer; Ozkaya, Ali Riza
    Non-peripherally tetra-2,6-dimethoxyphenoxy substituted Co(II) 3, Fe(II) 4, Mn(III) 5, and Ni(II) 6 phthalocyanines were prepared by refluxing the n-pentanol solution of their metal-free analogue H2Pc 2, (obtained by using 3-(2,6-dimethoxyphenoxy)phthalonitrile), metal salts (Co(CH3COO)2.4 H2O, Fe(CH3COO)2, Mn (CH3COO)2.4 H2O or NiCl2) and 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) as the catalyst under N2 atmosphere for 2 h. The molecular structure of metallophthalocyanines 3-6 were explained by common methods which are elemental analysis, MALDI-TOF mass, FTIR, and UV-Vis spectroscopies. The complexes are well dissolved in various solvents (dichloromethane, tetrahydrofuran, dimethylsulfoxide, dimethylformamide, and toluene. Electrochemical redox, electrocatalytic oxygen reducing and electrocolorimetric properties of the phthalocyanine complexes were also measured by voltammetric and in situ UV-Vis spectroelectrochemical techniques. The phthalocyanine complexes displayed highly reversible sequential one-electron redox processes occurring at metal and/or phthalocyanine ring. The association of these processes with net colour changes pointed out their functionality as electrochromic material. Furthermore, the phthalocyanine complexes 3-5 and especially Fe(II)Pc 4, showed striking electrocatalytic oxygen reducing activity, owing to the metal centres with redox activity, increasing their interplay with the O2 molecule.
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    Synthesis, characterization and investigation of the photophysical and photochemical properties of highly soluble novel metal-free, zinc(II), and indium(III) phthalocyanines substituted with 2,3,6-trimethylphenoxy moieties
    (Royal Soc Chemistry, 2015) Gurel, Ekrem; Piskin, Mehmet; Altun, Selcuk; Odabas, Zafer; Durmus, Mahmut
    This work presents the synthesis and characterization of metal-free, zinc((II)), and indium((III)) acetate phthalo-cyanines substituted with 2,3,6-trimethylphenoxy groups at the peripheral and non-peripheral positions. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of these novel phthalocyanines and un-substituted zinc((II)) and indium((III)) acetate phthalocyanines were investigated in dimethylformamide solution. The effects of the types of substituents and their positions and the variety of central metal ions on the phthalocyanine core on their spectroscopic, photophysical and photochemical properties were also determined. The studied 2,3,6-trimethylphenoxy substituted metal-free, zinc((II)) and indium((III)) acetate phthalocyanines especially indium((III)) acetate derivatives exhibited appropriate photophysical and photochemical properties such as high singlet oxygen generation and these phthalocyanines can be potential Type II photosensitizers for photodynamic therapy in cancer applications.
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    Synthesis, characterization, photophysical, and photochemical properties of novel zinc(II) and indium(III) phthalocyanines containing 2-phenylphenoxy units
    (Elsevier Science Bv, 2016) Ali, Haytham Elzien Alamin; Piskin, Mehmet; Altun, Selcuk; Durmus, Mahmut; Odabas, Zafer
    The synthesis of highly soluble and non-aggregated peripherally/non-peripherally Zn and In(OAc) phthalocyanines was achieved by 3-/ and 4-(2-phenylphenoxy)phthalonitrile as starting materials. The novel compounds were characterized by elemental analyses, FT-IR, H-1-NMR (for phthalonitriles), UV-vis and MALDI-TOF mass (for Pcs) spectroscopic techniques. Additionally, photophysical, photochemical and spectral properties of the phthalocyanines were reported. Especially, the indium(OAc) phthalocyanines showed good singlet oxygen quantum yields in DMSO and they can be appropriate candidates as Type II photosensitizers in photodynamic therapy (PDT) applications. (C) 2015 Elsevier B.V. All rights reserved.
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    The novel mesityloxy substituted metallo-phthalocyanine dyes with long fluorescence lifetimes and high singlet oxygen quantum yields
    (Elsevier Science Sa, 2016) Gurel, Ekrem; Piskin, Mehmet; Altun, Selcuk; Odabas, Zafer; Durmus, Mahmut
    The synthesis of novel peripheral or non-peripheral tetra-mesityloxy substituted metal-free, zinc and indium phthalocyanines, which are highly soluble in organic solvents, has been achieved. The phthalocyanines have been characterized by UV-vis, IR, MALDI-TOF Mass, H-1 NMR, C-13 NMR spectroscopies and elemental analysis. On their spectroscopic, photochemical and photophysical properties, the effects of the substituent position and the variety of central metal ions in phthalocyanine cavity are also investigated. Photodegradation, singlet oxygen and fluorescence quantum yields, and fluorescence lifetimes in dimethylformamide for the phthalocyanines are described. These properties of the compounds are very useful for photodynamic therapy applications and their high singlet oxygen quantum yields are very important for Type II mechanisms. The phthalocyanines can be appropriate candidates as Type II photosensitizers. (C) 2015 Elsevier B.V. All rights reserved.
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    Toluene vapor sensing characteristics of novel copper(II), indium(III), mono-lutetium(III) and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenoxy bioactive moieties
    (World Sci Publ Co Inc, 2018) Piskin, Mehmet; Can, Nursel; Odabas, Zafer; Altindal, Ahmet
    This study presents the synthesis, characterization and toluene sensing properties of copper(II), indium(III) acetate, mono-lutetium(III) acetate and tin(IV) phthalocyanines substituted with 2,6-dimethoxyphenol bioactive groups at the peripheral and non-peripheral positions. The effects of the substituent's position on the toluene vapor detection capabilities of these compounds were investigated. Adsorption data were analyzed by using first-order and Elovich equations in order to investigate the adsorption kinetics. It was found that the kinetics of the toluene adsorption strongly depends on the position of the substituent groups. Our results showed that the Elovich equation fits the experimental data well for non-peripherally substituted Pc based sensors, while the pseudo first-order model best describes the adsorption data for peripheral substituted Pc based sensors.