Synthesis and characterization of novel metal-free and metallo-porphyrazines with eight 3-thiopropylpentafluorobenzoate units

Abstract

Metal-free and metallo-porphyrazines (M=2H, Mg, Cu, Zn or Co) with eight polyfluorinated groups appended on the periphery through flexible alkylthio-bridges have been synthesized through esterification of octakis(hydroxypropylthio)porphyrazinato magnesium with 2,3,4,5,6-pentafluorobenzoic acid in the presence of dicyclohexylcarbodiimide (DCCI) and toluene-p-sulfonic acid. The symmetrically functionalized porphyrazines with eight ester units are soluble in common organic solvents, such as CHCl3, CH2Cl2, THF, acetone and toluene, and are insoluble in water and n-hexane. The newly synthesized compounds were characterized by FT-IR, UV–Vis, mass, 1H, 13C and 19F NMR, together with elemental analysis.