Synthesis and Spectral and Fluorescent Properties of Metal Complexes of Octakis(4-flurophenyl)tetraazaporphyrins

Abstract

Zn(II) octakis(4-fluorophenyl)tetraazoporphyrin and Cu(II) octakis(4-fluorophenyl)tetraazorphorphyrin were synthesized by the cyclization of bis(4-fluorophenyl)maleonitrile with zinc(II) and copper(II) chlorides. The geometry of Zn(II) octa(4-fluorophenyl)tetraazaporphyrin was optimized by the BioCharmm molecular mechanics method in the Hyperchem software package. Mg(II) octakis(4-fluorophenyl)tetraazaporphyrin was obtained by fusing bis(4-fluorophenyl)maleonitrile with metallic magnesium. Ni(II) octakis-(4-fluorophenyl)tetrazaporphyrin and Cu(II) octakis(4-fluorophenyl)tetrazaporphyrin were synthesized by the reaction of the fluoro-substituted magnesium complex with Ni(II) and Cu(II) chlorides in DMF. The synthesized compounds were identified by UV-Vis, 1H NMR spectroscopy, and mass spectrometry. The UV-Vis spectra of the Zn(II), Cu(II), Mg(II), and Ni(II) complexes were compared with those of Zn(II) octakis(4-methoxyphenyl)porphyrin and Mg(II) octakis(4-methoxyphenyl)porphyrin. The florescence spectra Zn(II) and Mg(II) octaphenyltetraazaporphyrins in chloroform solutions were measured, and the fluorescence quantum yields of the metal porphyrins were determined. Comparative analysis of the fluorescence quantum yields of molecules containing substituents with a large atomic weight was performed.