Synthesis and Spectral Properties of Halogen Substituted Copper(II) Tetraphenylporphyrins

Abstract

The exhaustive halogenation of the β-positions of Cu(II)-5,10,15,20-tetra-(2,6-difluorophenyl)porphyrin using N-bromosuccinimide and N-chlorosuccinimide in dimethylformamide was carried out. Cu(II)-β-octachloro-(2,3,4,5,6-pentafluorophenyl)porphyrin was synthesized by the reaction of Cu(II)-5,10,15,20-tetra-(2,3,4,5,6-pentafluorophenyl)porphyrin with N-chlorosuccinimide in dimethylformamide. Using the complexation of β-octabromo-5,10,15,20-tetra-(2,6-difluorophenyl)porphyrin, β-octachloro-5,10,15,20-tetra-(2,6-difluorophenyl)porphyrin, and β-octachloro-5,10,15,20-tetra-(2,3,4,5,6-pentafluorophenyl)porphyrin with copper salts in dimethylformamide under mild conditions, the corresponding copper(II) complexes were obtained. The coordination reaction kinetics of β-octabromo-5,10,15,20-tetra-(2,6-difluorophenyl-porphyrin with copper chloride in dimethylformamide has been studied. The kinetic parameters of the reaction were calculated. The obtained compounds were identified by UV-Vis and ¹H NMR spectroscopies, mass spectrometry, and elemental analysis. X-ray powder diffraction patterns were obtained for a number of copper complexes.