synthesis and characterization of a novel meso-porphyrin and its metallo derivatives

There has been a growing interest in the properties of substituted meso-tetraarylporphyrins and metallo porphyrins as catalysts for oxidation of hydrocarbons, oxygen detection, among others. This work describes the synthesis of a new porphyrin, 5,10,15,20-tetrakis(4-butoxy-3-methoxyphenyl)porphyrin, and its metallo complexes. Herein it was used a readily available reactant, vanillin, as starting material which was submitted to alkylation with n-bromobutane affording the synthetic precursor. The desired porphyrin was obtained by reacting the O-alkylated aldehyde with pyrrole in the presence of propionic acid (Alder-Longo method). The purified porphyrin was then subjected to the metallation process using iron (II) and manganese (II) salts. The synthesized compounds were characterized by IR, UV-Vis, NMR and EPR spectroscopy.