The functionality of hydroxypropylsulfanyl units of metal-free and metallo-porphyrazines, which are new compounds (M = 2H, Mg, Co, Cu or Zn), has been produced by esterification with a carboxylate group such as 2-fluoro-5-(trifluoromethyl)phenylacetic acid. The symmetrically functionalized porphyrazines, with eight ester units, are soluble in common organic solvents such as chloroform, dichloromethane, tetrahydrofuran, dimethylsulfoxide, acetone and toluene, and insoluble in water and n-hexane. Chloro-octakis[3-thiopropyl 2-fluoro-5-(trifluoromethyl)phenylacetate] porphyrazinato iron(III) (FePzCl) was prepared by the reaction of the metal-free porphyrazine and iron(II) acetate, followed by treatment with HCl solution. The monomeric bis-axial complex [FePz(py)(2)], as well as the bridged complex [FePz(pyz)](n), were formed as stable complexes by reacting FePzCl with pyridine and pyrazine, respectively. The novel compounds have been characterized by several spectroscopic techniques, such as FT-IR, UV-Vis, mass, H-1, C-13 and F-19 NMR, and elemental analysis. (C) 2013 Elsevier Ltd. All rights reserved.