Pinar Sen

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).

Tri-nuclear phthalocyanine complexes carrying N/O donor ligands as hydrogen peroxide catalysts, and their bleaching activity measurements by an online spectrophotometric method

Abstract A phthalocyanine (4) with four salicylhydrazone ligating groups that are directly linked through oxygen bridges to the macrocyclic core has been synthesized by condensation of tetrakis(4-formylphenoxy)phthalocyaninato zinc(II) (3) with salicylhydrazine. Salicylhydrazine was crystallized in methanol during the synthetic procedure. The crystal structure has triclinic space group P-1 with a = 5.8292(6) Å, b = 7.3039(7) Å, c = 17.9798(18) Å, α = 84.272(8)°, β = 89.184(8)°, γ = 81.469(8)°, and Z = 4. Intramolecular O–H⋯O and intermolecular O–H⋯O, N–H⋯N, N–H⋯O hydrogen bonds were determined in the crystal structure. In addition, there is a weak C–H⋯π interaction. Complexation on the periphery to yield tri-nuclear Zn(II)Pcs (5–7) was performed through the reaction of a Schiff base-substituted phthalocyanine (4) with MnCl2·4H2O, CoCl2·6H2O, or Ni(OAc)2 salts. Fourier transform infrared, 1H NMR, 13C NMR, UV–Vis, ICP-OES (inductively coupled plasma optical emission spectroscopy), mass spectroscopies, and elemental analyses were applied to characterize the prepared compounds. Bleach catalyst activity of the prepared phthalocyanine complexes (5–7) was examined by the degradation of morin and curcumin, respectively. The catalysts had better activity for color removing in solutions at ambient temperature than to that of tetraacetylethylenediamine (TAED).

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.

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.