Synthesis of a Novel Zinc(II) Porphyrin Complex, Halide Ion Reception, Catalytic Degradation of Dyes, and Optoelectronic Application

This work describes the synthesis of a novel zinc(II) porphyrin complex, namely [Meso-4 alpha-tetra-(1,2,3-triazolyl)phenylporphyrinato]zinc(II) symbolized by 4 alpha-[Zn(TAzPP)] (4), using the click chemistry approach in the presence of copper iodide. All of the synthetic porphyrin species reported herein were fully characterized by elemental analysis, infrared spectroscopy, proton nuclear magnetic resonance, UV-visible spectroscopy, and fluorescence. To synthesize the 4 alpha-[Zn(TAzPP)] complex (4), we produced 4 alpha-Meso-tetra-o-nitrophenylporphyrin (H2TNO2PP) and 4 alpha-meso-tetra-o-aminophenylporphyrin (4 alpha-H2TNH2PP) (1) using known classic literature methods. This 4 alpha atropisomer was converted to 4 alpha-meso-tetra-o-azidophenylporphyrin (4 alpha-H2TN3PP) (3) by reaction with sodium nitrite and sodium azide, and then it was metalated by Zn(II), leading to [4 alpha-meso-tetra(2-azidophenyl)porphyrinate]zinc(II) (4 alpha-[Zn(TN3PP)]) (3). The click chemistry synthetic method was finally used to prepare 4 alpha-[Zn(TAzPP)] (4). This new tetracoordinated zinc(II) porphyrin complex was prepared and characterized in order to: (i) produce a receptor for anion recognition and sensing application for Cl- and Br-; (ii) study the catalytic decomposition of rhodamine B (RhB) and methyl orange (MO) dyes; and (iii) determine the electronic characteristics as a photovoltaic device. Complex (4) formed 1:1 complex stoichiometric species with chloride and bromide halides and the average association constants of the 1:1 addicts were similar to 10(3). The photodecomposition of RhB and MO dyes in the presence of complex (4) as a catalyst and molecular oxygen showed that complex (4) presented a photodegradation yield of approximately 70% and could be reused for five successive cycles without any obvious change in its catalytic activity. The current-voltage characteristics and impedance spectroscopy measurements of complex (4) confirmed that our zinc(II) metalloporphyrin could be used as a photovoltaic device.