Armağan Günsel

Comparative studies of photophysical and electrochemical properties of sulfur-containing substituted metal-free and metallophthalocyanines

The synthesis, photophysical and electrochemical properties of soluble sulfur-containing 4-(methylthio) benzenethiol substituted, non-peripherally metal-free and metallo (Zn, Ga, Co, and Mn) phthalocyanine complexes (2–6) are reported for the first time. The new phthalocyanines have been characterized by FT-IR spectroscopy, 1H-NMR, 13C-NMR, mass and UV–Vis spectroscopy techniques. Spectroscopic properties of these compounds were investigated in different solvents. Spectral and photophysical (fluorescence quantum yield) properties of metal free (2), zinc(II) (3), and gallium(III) phthalocyanines (4) were reported in different solvents toluene, tetrahydrofuran, and dimethyl sulfoxide. These results suggest that the solvents play role on the fluorescence quantum yields ΦF of the synthesized complexes (2–4). The electrochemical studies exhibit that while complexes (3) and (4) give only Pc ring-based redox processes, complexes (5) and (6) give both metal and ring-based redox reactions due to the energy level of metal in the Pc core lie between the HOMO and the LUMO of the ring.

Novel type ketone-substituted metallophthalocyanines: synthesis, spectral, structural, computational and anticancer studies

This work reports on the synthesis and characterization of phthalocyanines (M = Cu(II) (2), Zn(II) (3) In(III) (4) and Co(II) (5)) peripherally tetra-substituted with 1-(4-hydroxyphenyl)propan-1-one. Confirmation of the synthesized phthalocyanine structures are performed with a combination of elemental analysis, FTIR, 1H-NMR, 13C-NMR, UV-vis and MALDI-MS SEM and spectral data. Their aggregation properties were examined in THF by UV-vis. Spectral and photophysical (fluorescence quantum yield) properties of complexes (2–4) were reported in THF (tetrahydrofuran). These results suggest that the metal in the core of the phthalocyanine plays an important role in the fluorescence quantum yields ΦF of the synthesized complexes (2–4). Also, the anticancer activities of complexes were studied on MCF-7, MG63, and L929 cell lines. Finally, all synthesized phthalocyanines were investigated by quantum chemical studies. Chemical reactivity parameters such as EHOMO, ELUMO, ΔE (HOMO–LUMO energy gap) were calculated by Gaussian software.

Axially phenoxy-derivative disubstituted phthalocyanine: synthesis, characterization and photophysical properties

We report the highly soluble axially disubstituted 4-(methoxymethyl) phenol silicon (IV) (1) phthalocyanine which was synthesized by the reaction of silicon phthalocyanine dichloride (SiPcCl2) with 4-(methoxymethyl)phenol. UV–Vis, FT-IR, 1H, 13C, NMR and mass spectrometry were used to characterize SiPc (1). Fluorescence quantum yield (spectral and photophysical) characteristics of SiPc (1) were investigated for various solvents. The obtained spectral and photophysical results indicated that the fluorescence quantum yields (ΦF) of SiPc (1) are both lower than unsubstituted ZnPc and SiPcCl2 in the solvents used which is not typical of silicon-phthalocyanines. The effects on optoelectronic and spectral properties of SiPc (1) of solvents and concentrations were investigated in detail. We obtained absorption band edge, maximum peak of absorbance, molar and mass extinction coefficients, refractive index, optical band gap, optical and electrical conductance of SiPc (1) for different solvents and concentrations. We obtained the refractive index values of SiPc (1) with many relationships. Also, we investigated the angles of incidence and refraction of SiPc (1). SiPc (1) exhibited semiconductor behavior in terms of optical band gap and can be used for photonic applications.Graphical Abstract

Synthesis, characterization, and optical and surface properties of (4-(trifluoromethylthio)phenoxy) copper(II) phthalocyanine

This paper reports on the synthesis and characterization of a non-peripherally tetra-substituted copper phthalocyanine containing a 4-(trifluoromethylthio)phenoxy group. The synthesized compounds have been characterized using elemental analysis, FTIR, 1H NMR, 13C NMR, MALDI-TOF, SEM and UV-vis spectral data. The crystal structure of 3-(4-(trifluoromethylthio)phenoxy)phthalonitrile (1) was confirmed by single-crystal X-ray diffraction. The crystallographic information file (cif) was uploaded to the data center with CCDC 1538643. We investigated the UV-vis spectra, band edge, band gap, refractive indices, dispersion, sensing, conductance and dielectric properties. The surface morphological properties of the Cu(II)Pc (2) film were investigated under different conditions.

Synthesis, characterization, antioxidant and antibacterial properties of non-peripherally and peripherally tetra-substituted phthalocyanines

abstract This study focuses on the synthesis, spectral, antioxidant and antibacterial properties of the metal-free, zinc and cobalt phthalocyanines (3–8) bearing 4-methoxy-phenoxy substituents on the nonperipheral [(1(4), 8(11), 15(18), 22(25)] or peripheral [2(3), 9(10), 16(17), 23(24)] positions. The new synthesized complexes 7 and 8 have been characterized by elemental analysis, FT-IR, MALDI-MS, and UV-vis spectral data. The antioxidant activities of all tested compounds were investigated by applying three different antioxidant methods such as radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl, chelating ability to ferrous ions and reducing power activity methods. In addition, the antibacterial activities of the compounds were screened by disc diffusion method against one gram-negative and four gram-positive bacteria. The tested phthalocyanine compounds showed very good antioxidant activity and promising antibacterial properties.

Highly soluble tetrasubstituted lanthanide bis-phthalocyanines; synthesis, characterization, electrical properties and aggregation studies

We report the synthesis, characterization and electrical properties of lanthanide metal based bis-phthalocyanines, {M[Pc-(β-HHT)4]2} (HHT:1-hydroxyhexane-3-ylthio){M = Lu3+(2), Eu3+(3), and Yb3+(4)}. The interaction of bis-phthalocyanines with Ag+ and Pd2+ metal ions were investigated by UV-vis spectroscopy and atomic force microscopy. Thin films of bis-phthalocyanine molecules were prepared by spin-coating method. The surface morphology of thin films were performed with Atomic Force Microscopy as further investigate. The electrical transport properties of ITO/Pc/Al devices were investigated. At low voltages all the films showed an ohmic conduction, whereas at higher voltage levels the conduction is dominated by space charged limited conduction with exponential distribution of trapping levels. Measurements of current density as a function of inverse temperature at constant applied voltage yielded a hole mobility values, μp = 2.12 × 10−7, 6.72 × 10−7 and 1.58 × 10−6 m2.sn−1.V−1 for lanthanium phthalocyanines. From the analysis of frequency, ω, dependence of electrical conductivity, σac. it was found that the σac obeys the power law given by σac = Aωs, in which the frequency exponent “s” decreases with temperature.