Metal-free, metallo-, oligomeric, and monomeric porphyrazine complexes of (3-thiopropyl anthraquinone-2-carboxylate) units

Abstract

Metal-free and several metallo-porphyrazines (M = Mg, 2H, Co, Cu, or Zn) carrying eight (3-thiopropyl anthraquinone-2-carboxylate) groups at the peripheral positions were synthesized from octakis(3-hydroxypropylthio)porphyrazinato] Mg(II). Symmetrically functionalized porphyrazines with eight ester units were soluble in common organic solvents. Chloro-octakis(3-thiopropyl anthraquinone-2-carboxylate) porphyrazinato iron(III) (FePzCl) was prepared by the reaction of metal-free porphyrazine with iron(II) acetate and further treatment with hydrochloric acid solution. The oligomeric structure [FePz(pyz)]n and the monomeric compound [FePz(py)2] were formed as stable complexes by reacting FePzCl with pyrazine and pyridine, respectively. The porphyrazine compounds were characterized by different spectroscopic methods.