Synthesis of p -substituted tetraphenylporphyrins and corresponding ferric complexes with mixed-solvents method

Abstract

By using mixed-solvents method, five kinds of p-substituted tetraphenylporphyrin compounds [T(p-R)PPH₂, R=NO₂, Cl, CH₃, OCH₃, OH] were synthesized by the condensation of p-substituted benzaldehyde with pyrrole in mixed solvents (propionic acid, acetic acid and nitrobenzene), and corresponding ferric complexes [T(p-R)PPFe^IIICl] were synthesized in dimethylformamide. The above free base porphyrins were obtained in 30%–50% yields, metalation yields were up to 90% and total yields of ferric complexes were 27%–50%. Effects of reactive conditions, solvents and oxidants on yields of free base porphyrins were investigated and the relevant mechanism was discussed. Structures of the above porphyrin complexes were characterized by ultraviolet-visible (UV-Vis), infrared (IR) and far infrared (FIR) spectroscopy.