Göknur Yaşa Atmaca

Novel axially carborane-cage substituted silicon phthalocyanine photosensitizer; synthesis, characterization and photophysicochemical properties

The novel axially dicarborane substituted silicon (IV) (SiPc-DC) phthalocyanine was synthesized by treating silicon phthalocyanine dichloride SiPc(Cl)2 (SiPc) with o-Carborane monool. The compound was characterized by mass spectrometry, UV-Vis, FT-IR, (1)H and (11)B Nuclear Magnetic Resonance Spectroscopy (NMR). Spectral, photophysical (fluorescence quantum yield) and photochemical (singlet oxygen (ΦΔ) and photodegradation quantum yield (Φd)) properties of the complex were reported in different solutions (Dimethyl sulfoxide (DMSO), Dimethylformamide (DMF) and Toluene). The results of spectral measurements showed that both SiPc and carborane cage can have potential to be used as sensitizers in photodynamic therapy (PDT) and boron neutron capture therapy (BNCT) by their singlet oxygen efficiencies (ΦΔ=0.41, 0.39).

The Synthesis, Characterization, Crystal Structure and Photophysical Properties of a New Meso-BODIPY Substituted Phthalonitrile.

A new highly fluorescent difluoroboradipyrromethene (BODIPY) dye (4) bearing an phthalonitrile group at meso-position of the chromophoric core has been synthesized starting from 4-(4-meso-dipyrromethene-phenoxy)phthalonitrile (3) which was prepared by the oxidation of 4-(2-meso-dipyrromethane-phenoxy)phthalonitrile (2). The structural, electronic and photophysical properties of the prepared dye molecule were investigated. The final product exhibit noticeable spectroscopic properties which were examined by its absorption and fluorescence spectra. The original compounds prepared in the reaction pathway were characterized by the combination of FT-IR, 1H and 13C NMR, UV–vis and MS spectral data. It has been calculated; molecular structure, vibrational frequencies, 1H and 13C NMR chemical shifts and HOMO and LUMO energies of the title compound by using B3LYP method with 6-311++G(dp) basis set, as well. The final product (4) was obtained as single crystal which crystallized in the triclinic space group P-1 with a = 9.0490 (8) Å, b = 10.5555 (9) Å, c = 11.7650 (9) Å, α = 77.024 (6)°, β = 74.437 (6)°, γ = 65.211 (6)° and Z = 2. The crystal structure has intermolecular C—H···F weak hydrogen bonds. The singlet oxygen generation ability of the dye (4) was also investigated in different solvents to determine of using in photodynamic therapy (PDT).

Novel sulfonated hydrophilic indium(III) and gallium(III) phthalocyanine photosensitizers: preparation and investigation of photophysicochemical properties

Abstract The new tetra-non-peripherally benzenesulfonic acid-substituted hydrophilic gallium chloride and indium chloride phthalocyanine complexes have been synthesized by cyclotetramerization of 4-(2,3-dicyanophenyl)benzenesulfonic acid (1). The newly synthesized phthalocyanines have been characterized by Fourier transform infrared spectroscopy, proton nuclear magnetic resonance, mass and UV–vis spectroscopy techniques. The water-soluble gallium(III) phthalocyanine derivative (2) was aggregated in aqueous media but was fully disaggregated in the presence of a surfactant Triton X-100. The incorporation of sulfonate moieties of the phthalocyanine macrocycle provides hydrophilic character to the new compounds, which is useful for drug administration and serves as crucial in PDT application. So, the photochemical properties (singlet oxygen quantum yields and photodegradation quantum yields) and photophysical properties (fluorescence behavior) of the complexes were reported in different solutions (DMSO and water). The results of spectral measurements showed that both np-GaPc (2) and np-InPc (3) can be used as sensitizers in PDT because of their singlet oxygen efficiencies.

Novel peripherally substituted zinc phthalocyanine: synthesis, characterization, investigation of photophysicochemical properties and theoretical study

Abstract The new thiohexanoic acid substituted zinc phthalocyanine was synthesized and characterized by FT-IR, 1H–NMR, electronic spectroscopy, and mass spectrometry as well as DFT calculation studies. The photochemical properties (singlet-oxygen quantum yields and photodegradation quantum yields) and photophysical properties (fluorescence quantum yields and fluorescence behavior) of the compound were studied in dimethylsulfoxide (DMSO), dimethylformamide (DMF) and tetrahydrofuran (THF). Singlet-oxygen quantum yields ranged from 0.29 to 0.43. However, energy-minimized structure, vibrational frequency, electronic distribution and molecular orbitals were obtained by DFT calculations which were supported by experimental results.

Synthesis, photophysics, and photochemistry of peripherally Schiff base-zinc complex substituted zinc phthalocyanine

Abstract The content of this work is based on the introduction of the salicylhydrazone-zinc complexes into the phthalocyanine core. The reaction of the salicylhydrazone substituted ZnPc (1) with the related zinc(II) salt in basic conditions in DMF yielded bis[bis(salicyhydrazone)phenoxy)zinc(II)] phthalocyaninato zinc(II) (5) in which two salicylhydrazone-Zn complexes are linked through oxygen bridges to the macrocyclic core as three-nuclear complex. The novel compound synthesized in this study was fully characterized by general spectroscopic techniques such as FT-IR, UV-vis, 1H NMR, 13C NMR, elemental analysis and mass spectroscopy. In addition, spectral, photophysical (fluorescence quantum yields), and photochemical (generation of singlet oxygen and photo stability under light irradiation) properties of newly synthesized phthalocyanine (5) and the starting Pcs molecules used to obtain this molecule were investigated in DMSO solutions, comparatively.

Synthesis, characterization of new phthalocyanines and investigation of photophysical, photochemical properties and theoretical studies

This work describes the synthesis, spectral, aggregation and fluorescence properties of bis 4-[(4-tert-butylbenzyl)oxy substituted metal free (2), magnesium (3), zinc (4) and nickel (5) phthalocyanines. The syntheses of the novel compounds were confirmed by FT-IR, UV-vis, mass and NMR spectroscopy techniques, as well as elemental analysis. The effects of the nature of the central metal on the photophysical parameters of the phthalocyanine complexes are reported in this study. The photochemical properties (singlet oxygen quantum yields and photodegradation quantum yields) and photophysical properties (fluorescence behavior and fluorescence quantum yield) of the complexes were reported in different solutions (dimethyl sulfoxide (DMSO) and dimethyl formamide (DMF) and tetrahydrofuran (THF)). However, energy minimized structure, vibrational frequency, molecular orbital levels and electronic absorption spectra were obtained by DFT calculations which supported the experimental results.

Five-nuclear phthalocyanine complex bearing terpyridine zinc complex: Synthesis, and photophysicochemical studies

The context of this study is based on the synthesis of tetrakis{4-(2-([2,2′:6′,2′′-terpyridine]Zn(II)-4′-yl(methyl)amino)ethoxy)}phthalocyaninato zinc (II) (3) bearing four terpyridine-Zn(II) complexes that are directly linked through oxygen bridges to the macrocyclic core in order to create new supramolecular assemblies. The target phthalocyanine (3) was obtained by cyclotetramerization reaction of terpyridine-Zn (II) complex substituted phthalonitrile (2). All novel compounds synthesized in this study were fully characterized by general spectroscopic techniques such as FT-IR, UV-vis, and 1H-NMR, 13C-NMR, elemental analysis and mass spectroscopy. Spectral, photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen production and photodegradation under light irradiation) properties of newly synthesized phthalonitrile (2) and its phthalocyanine derivative (3) as five nuclear phthalocyanine were investigated in DMSO solutions.

Novel, Highle Soluble Non-Peripherally Phthalocyanines Bearing Bulky Groups Containing Fluorine Atoms: Synthesis, Characterization, Spectral and Improved Photophysicochemical Properties

Bu çalışmada yeni 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10 3-nitroftalonitril ve onun çözünebilir non-peripheral çinko (II) (2), magnezyum (II) (3), kobalt (II) (4) ve indiyum klorür (III) (5) ftalosiyanin türevlerinin sentezi ilk kez rapor edildi. Yeni sentezlenmiş metalo ftalosiyanin türevlerinin yapıları, kütle, UV-Vis, FT-IR, ve 1H-NMR spektroskopisi kullanılarak karakterize edildi. Fotokimyasal (Singlet Oksijen foto bozunma kuantum verimleri) ve fotofiziksel (floresans kuantum verimleri) özellikleri tetrahidrofuran (THF) içinde incelendi. Flor atomları taşıyan uzun alkil zincirli gruplar taşıyan metallo fitalosiyaninlerin (2-5), THF, diklorometan (DCM), kloroform (CHCI3) ve toluen gibi bilinen organik çözücülerde yığılma göstermeden yüksek çözünürlüğe sahip oldukları görüldü. Bunun yanı sıra, merkez metal iyon türü ve substitüentin pozisyon etkisi daha önceki çalışmalarla karşılaştırılarak çalışıldı. Non peripheral konumun fotofiziksel ve fotokimyasal özellikleri geliştirdiği gözlendi.