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Öğe Electrochemical, Spectroelectrochemical, and Electrocatalytic Dioxygen Reducing Properties of Peripheral Tetra-2,6-dimethoxyphenoxy Substituted Phthalocyanines(John Wiley and Sons Inc, 2021) Orman, Efe Baturhan; Pişkin, Mehmet; Odabaş, Zafer; Özkaya, Ali RızaBy using of peripherally tetrakis-2,6-dimethoxyphenoxy substituted Co(II), Fe(III), and Mn(III) phthalocyanines was observed to extend the redox richness of the phthalocyanine ring with the addition of reversible metal-based electron transfer couples to the phthalocyanine ring-based electron transfer processes in solution. The emergence of highly steady anionic and cationic redox species with clear spectral and colour changes both in solution and in the film during in situ spectroelectrochemical and in situ electrocolorimetric measurements pointed out their applicability as electrochromic materials. Furthermore, the phthalocyanine complexes demonstrated strong interaction with dioxygen and thus, high electrocatalytic enforcement for its reduction.Öğe Newly Soluble and Non-Aggregated Copper(II) and Tin(II) Phthalocyanines: Synthesis, Characterization and Investigation of Photophysical and Photochemical-Responsive(2017) Pişkin, Mehmet; Öztürk, Ömer Faruk; Odabaş, ZaferThis work presents the synthesis and characterization of non-aggregated and highly soluble copper(II) and tin(II) phthalocyaninessubstituted with 2,6-dimethoxyphenoxy groups at the non-peripheral (alpha) and peripheral (beta) positions. The phthalocyanines havebeen characterized by common spectroscopic techniques. They show excellent solubility and non-aggregated species in common organicsolvents such as dimethylsulfoxide, dimethylformamide, tetrahydrofuran, toluene, acetonitrile, chloroform and dichloromethane, whichmake them candidates to use for many applications in different fields of science and technology. The effects positions of substituenton the phthalocyanine skeleton and the variety of central metal ions on the phthalocyanine of aggregation and on their spectroscopicproperties were determined in different solvents as mentioned above. The novel synthesized copper phthalocyanines were not evaluatedfor fluorescence, photophysical and photochemical properties due to transition metal and paramagnetic behavior of central metalin the phthalocyanine cavity. The effects of substituent and their positions on the tin(II) phthalocyanines’ on their photophysical(fluorescence quantum yields and lifetimes) and photochemical properties (singlet oxygen generation and photodegradation underlight irradiation) were also investigated and reported in dimethylsulfoxide for the first time.Öğe Synthesis and Spectroscopic Properties of Newly Tetrapyrazinoporphyrazine Containing Gadolinium(III) Acetate(2023) Pişkin, Mehmet; Odabaş, Zafer; Durmuş, MahmutA new tetrakis-(2-methylpyrazino)porphyrazinato gadolinium(III) acetate complex was synthesized. Elemental analysis, Fourier-Transform Infrared, Ultraviolet-visible, and fluorescence spectroscopy techniques clarified its structure. It can dissolve very well without aggregation in both Dimethyl sulfoxide and N, N-Dimethylformamide, which have high dielectric constant and high dipole moment from polar aprotic solvent type. Its aggregation property was also investigated in dimethyl sulfoxide at different concentrations, and it was determined to contain monomeric species. In addition, its fluorescence properties were investigated in Dimethyl sulfoxide and the effect of gadolinium(III) acetate metal ion as a heavy rare earth element was determined. According to the findings in this study, it may be used as an electronic and optical material and in various technological applications such as photocatalytic applications. In addition, these findings may be useful for systems that include changes in pyrazinoporphyrazine-like forms.Öğe Synthesis, molecular, and photophysicochemical characterizations of phthalocyanine dyes containing sodiumsulfonatenaphthalen-2-olate groups(Elsevier, 2025) Saruhan, Serkan; Pişkin, Mehmet; Özturk, Ömer Faruk; Odabaş, ZaferIn this study, novel highly water-soluble 6-sodiumsulfonatenaphthalen-2-olate substituted phthalocyanines from the organic near-infrared dye class and contained zinc(II) or indium(III) metal ions in their cavity, were designed, and synthesized to explore their potential use as photosensitizers in photodynamic therapy. The molecular structures of the starting materials and dyes were characterized using elemental analysis, FT-IR, UV-vis, 1H-NMR, 13C-NMR, and MALDI-TOF mass spectrometry. The solubility and aggregation behaviors of these phthalocyanine dyes have been investigated in polar solvent types such as dimethylsulfoxide and N,Ndimethylformamide, ethanol, methanol, and water, as well as in phosphate-buffered saline. They have high solubility in the studied solvents and do not show any tendency to aggregate, except for water. Their photophysical and photochemical properties were investigated in N,N-dimethylformamide. The influence of the presence and position of substituents on their macrocyclic and the nature of the metal species in their cavities on their photophysical and photochemical parameters were reported. The fluorescence properties of the zinc(II) dyes studied were enhanced, while those of indium(III) dyes were low but sufficient as photosensitizers. The suitable and sufficient photophysicochemical properties of the water-soluble near-infrared new phthalocyanine dyes denote they can be potential candidates as Type II photosensitizers for photocatalytic applications.Öğe Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine(2021) Pişkin, Mehmet Burçin; Öztürk, Ömer; Odabaş, Zafer2(3),9(10),16(17),23(24)-tetrakis-2,6-dimethoxyphenoxy substituted magnesium (II) phthalocyanine, which has very good solubility in polar and non-polar solvents and does not aggregate, was synthesized. Its structure was characterized by spectroscopic methods such as elemental analysis, UV-vis, FT-IR, MALDI-TOF mass and 1H NMR. It has very good solubility in polar aprotic solvents such as dimethyl sulfoxide, N, N- Dimethylformamide, tetrahydrofuran, dichloromethane, and non-polar solvents such as toluene, chloroform. Its aggregation properties have been studied both in the solvents mentioned above and in N, N- Dimethylformamide at different concentrations. Its photophysical properties were determined in N, N-dimethyl formamide. The effects of the nature and presence of 2,6-dimethoxyphenoxy group, which is an antioxidant derivative, on the phthalocyanine skeleton on the spectroscopic and photophysical properties were investigated by comparing it with unsubstituted magnesium (II) phthalocyanine. It can be a good nominee for various technological applications in that it does not aggregate and has good solubility in polar and non-polar solvents, as well as better and favorable fluorescence properties than its analog in the previous study.Öğe Yeni İyi Çözünür ve Agregasyon Yapmayan Bakır II ve Kalay II MetallibFtalosiyaninler: Sentez, Karakterizasyon ve Fotofiziksel ve Fotokimyasal Duyarlılığın Araştırılması(Zonguldak Bülent Ecevit Üniversitesi, 2017) Pişkin, Mehmet; Öztürk, Ömer Faruk; Odabaş, ZaferBu çalışma, non-periferal alfa- ve periferal beta- pozisyonlarda 2,6-dimetoksi gruplarıyla sübstitüe edilen agrege olmayan oldukça çözünür bakır II ve kalay II metalli ftalosiyanin bileşiklerinin sentezini ve karakterizasyonunu sunar. Bu ftalosiyaninler bilinen spektroskopik tekniklerle karakterize edilmiştir. Dimetilsülfoksit, dimetilformamit, tetrahidrofuran, toluen, asetonitril, kloroform ve diklorometan gibi bilinen organik çözücülerde mükemmel çözünürlük ve agregasyon yapamayan türler göstermiştir. Orijinal ftalosiyanin bileşiklerinin yüksek çözünürlük özellikleri ve agregasyon yapmayan türler içermesi onları bilim ve teknolojinin farklı alanlarında pek çok uygulamalarda kullanılmaları amacıyla aday yapar. Bu orjinal ftalosiyaninlerin spektroskopik özellikleri hakkında üstte bahsedilen farklı çözeltilerde ftalosiyanin merkezindeki farklı metal iyonlarının ve ftalosiyanin iskeleti üzerinde sübstitüentin pozisyon etkileri ve agregasyon özellikleri belirlenmiştir. Ayrıca, bileşiklerin dimetilsülfokit çözeltisinde farklı konsantrasyonlardaki agregasyon özellikleri de incelenmiştir. Yeni sentezlenen bakır metalli ftalosiyaninler, ftalosiyanin çekirdeğinde merkez metalinin paramagnetik davranışı ve geçiş metalinden dolayı floresans, fotofiziksel ve fotokimyasal özellikleri değerlendirilmedi. Alfa ve betasübstitüentli kalay II metalli orijinal ftalosiyanin bileşiklerinin fotofiziksel floresans kuantum verimleri ve ömürleri ve fotokimyasal özellikleri singlet oksijen kuantum verimleri, fotobozunma kuantum verimleri hakkında ftalosiyanin iskeleti üzerindeki sübstitüent ve sübstitüentin pozisyonlarının etkileri de ilk defa bu çalışmada incelenmiş ve rapor edilmiştir [EN] This work presents the synthesis and characterization of non-aggregated and highly soluble copper II and tin II phthalocyanines substituted with 2,6-dimethoxyphenoxy groups at the non-peripheral alpha and peripheral beta positions. The phthalocyanines have been characterized by common spectroscopic techniques. They show excellent solubility and non-aggregated species in common organic solvents such as dimethylsulfoxide, dimethylformamide, tetrahydrofuran, toluene, acetonitrile, chloroform, dichloromethane, which makes them candidates to use for many applications in different fields of science and technology. The effects positions of substituent and aggregation on the phthalocyanine skeleton and the variety of central metal ions on the phthalocyanine core on their spectroscopic properties of the novel phthalocyanines were determined in different solvents as mentioned above. The novel synthesized copper phthalocyanines were not evaluated for fluorescence, photophysical and photochemical properties due to transition metal and paramagnetic behavior of central metal in the phthalocyanine cavity. The effects of substituent and their position on the phthalocyanine skeleton on the tin II phthalocyanines’s photophysical fluorescence quantum yields and lifetimes and photochemical properties singlet oxygen generation and photodegradation under light irradiation were also investigated in dimethylsulfoxide for the first time. The obtained results for tin II phthalocyanines were also compared with unsubstituted zinc II phthalocyanine for determination of substitution effect and central metal effect on photophysical and photochemical properties in dimethylsulfoxide.Öğe Yeni Mono-Lutesyum Iıı Ftalosiyaninlerin Sentezi, Karakterizasyonu ve Spektroskopik Özellikleri(Zonguldak Bülent Ecevit Üniversitesi, 2016) Pişkin, Mehmet; Odabaş, ZaferBu çalışmada çeşitli teknolojik uygulamalarda kullanılması amacıyla yeni, oldukça çözünür ve agregasyon yapmayan ftalosiyanin halkasına periferal ve non-periferal pozisyonlardan 2,6-dimetoksifenoksi gruplarıyla tetrasübstitüe lutesyum III asetat metalli ftalosiyanin bileşikleri sentezlenmiş ve yapıları elemental analiz, FT-IR, 1H NMR, UV–vis spektroskopisi ve MALDI-TOF Kütle analiz metotları kullanılarak karakterize edilip aydınlatılmıştır. Ayrıca bu bileşiklerin periferal ve non-periferal pozisyonlardan 2,6-dimetoksifenoksi gruplarıyla sübstitüe edilmesiyle spektroskopik özelliklerindeki değişiklikler rapor edilmiştir [EN] In this study, the novel, highly soluble and non-aggregated peripherally /non-peripherally tetrakis-2,6-dimethoxyphenoxy substituted lutetium III acetate mono-phthalocyanine complexes have been synthesized for use in different technological applications in this study. The new phthalocyanine complexes have been characterized by elemental analysis, IR, 1H NMR, UV–vis spectroscopy and MALDI-TOF Mass spectra. The effects of the positions peripheral or non-peripheral of the substituents on the spectroscopic properties of 2,6-dimethoxyphenoxy substituted mono-lutetium III phthalocyanines have been also reported.
