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    Halogen-substituted zinc(II) phthalocyanines: Spectral properties and structure of thin films
    (Elsevier, 2022) Klyamer, Darya; Bonegardt, Dmitrya; Krasnov, Pavel; Sukhikh, Aleksandr; Popovetskiy, Pavel; Khezami, Khaoula; Durmuş, Mahmut; Basova, Tamara
    In this work, the effect of the type of halogen substituents on the structure, morphology, and conductivity of thin films of zinc(II) phthalocyanines ZnPcHal4 (Hal = F, Cl, Br, I), deposited both by evaporations in vacuum and by a spin coating technique was studied. The influence of these different halogen substituents on the spectral properties of ZnPcHal4 derivatives was also investigated. For this purpose, the density-functional theory calculations of the vibrational spectra of ZnPcHal4 were carried out. It was shown that ZnPcHal4 (Hal = F, Cl) films obtained by physical vapor deposition (PVD) were polycrystalline and consisted of well-distinguishable rounded grains, whereas the introduction of the bulk bromine and iodine substituents led to the formation of amorphous films both in the PVD process and during spin coating deposition. The lateral d.c. conductivity of the films was shown to decrease in the order ZnPcCl4 > ZnPcF4 > ZnPcBr4 > ZnPcI4. The conductivity of PVD films, which were characterized by higher crystallinity and order, was higher than that of spun films. © 2022 Elsevier B.V.
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    Synthesis and Characterization of New-Type Soluble ?-Substituted Zinc Phthalocyanine Derivative of Clofoctol
    (Mdpi, 2023) Dridi, Sabrine; Khiari, Jamel Eddine; Magna, Gabriele; Stefanelli, Manuela; Lvova, Larisa; Mandoj, Federica; Khezami, Khaoula
    In this work, we have described the synthesis and characterization of novel zinc (II) phthalocyanine bearing four 2-(2,4-dichloro-benzyl)-4-(1,1,3,3-tetramethyl-butyl)-phenoxy substituents on the peripheral positions. The compound was characterized by elemental analysis and different spectroscopic techniques, such as FT-IR, H-1 NMR, MALDI-TOF, and UV-Vis. The Zn (II) phthalocyanine shows excellent solubility in organic solvents such as dichloromethane (DCM), n-hexane, chloroform, tetrahydrofuran (THF), and toluene. Photochemical and electrochemical characterizations of the complex were performed by UV-Vis, fluorescence spectroscopy, and cyclic voltammetry. Its good solubility allows a direct deposition of this compound as film, which has been tested as a solid-state sensing material in gravimetric chemical sensors for gas detection, and the obtained results indicate its potential for qualitative discrimination and quantitative assessment of various volatile organic compounds, among them methanol, n-hexane, triethylamine (TEA), toluene and DCM, in a wide concentration range.
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    Synthesis, characterization, photophysical, and photochemical properties of novel phthalocyanines containing thymoxy groups as bioactive units
    (Springer, 2023) Atajanov, Rovshen; Khezami, Khaoula; Durmus, Mahmut; Odabas, Zafer
    In this study, new 4-chloro-5-(2-isopropyl-5-methylphenoxy)phthalonitrile compound, containing bioactive thymoxy group, and its metal-free phthalocyanine and metallo-phthalocyanine derivatives were synthesized for the first time. Their structures were determined by spectroscopic methods such as FTIR, UV-Vis, H-1-, and C-13-NMR (for phthalonitrile derivative), MALDI-TOF mass spectrometry (for phthalocyanine derivatives) and elemental analysis as well. The phthalocyanines showed excellent solubility in polar and nonpolar solvents without aggregation and absorb at long wavelengths with their high molar coefficient. In N,N-dimethylformamide, the effects of the type of central metal ions [metal-free, indium(III) acetate, lutetium(III) acetate, magnesium(II) or zinc(II)] in the phthalocyanine, containing bioactive thymoxy group, cavity on the spectroscopic, photophysical, and photochemical properties of the phthalocyanines were determined. These features are compared with each other. Lutetium(III) acetate phthalocyanine did not show any fluorescence, while metal-free phthalocyanine and indium(III) acetate phthalocyanine showed low fluorescence. It was determined that magnesium phthalocyanine significantly enriched the fluorescence, and zinc phthalocyanine had appropriate and sufficient fluorescence. Lutetium(III) acetate and zinc(II), especially indium(III) acetate phthalocyanines, could produce large amounts of singlet oxygen. Metal-free and magnesium phthalocyanines had the capacity to produce sufficient singlet oxygen (it means production of enough amount of singlet oxygen by a photosensitizer candidate during PDT applications). All phthalocyanines have sufficient and suitable photostability (it means an ideal photosensitizer should be stable under light irradiation until complete its PDT activation, and it should be decomposed after its PDT activation so that it does not accumulate in the body). With these determined properties, magnesium(II), especially indium(III) acetate and zinc(II) phthalocyanines, may be suitable candidates as type II photosensitizers for photodynamic therapy applications. Lutetium(III) acetate phthalocyanine may be a photosensitizer candidate in photocatalytic applications.