Metallo-porphyrazines with eight [5-thiopentyl 3,4,5-tris(benzyloxy)benzoate] groups: Synthesis, characterization, aggregation, and solubility behavior

Metal-free and metallo-porphyrazines having eight 5-hydroxypentylthio units at the peripheral positions have been prepared from 2,3-bis(5-hydroxypentylthio)maleonitrile. By the esterification reaction of magnesium hydroxy-porphyrazine with 3,4,5-tris(benzyloxy)benzoic acid in dicyclohexylcarbodiimide and toluene-p-sulfonic acid, the reactivity of the hydroxypentyl units was indicated. On the other hand, iron porphyrazine derivatives with eight [5-thiopentyl 3,4,5-tris(benzyloxy)benzoate] groups attached to the periphery positions were synthesized. By the reaction of metal-free porphyrazine with iron (II) acetate and further processing with HCl solution, FePzCl was obtained. Finally, by reacting FePzCl with pyridine or pyrazine, [FePz(py)(2)] and [FePz(pyz)](n) complexes were prepared, respectively. The characterizations of target complexes were carried out by utilizing different spectroscopic methods such as FT-IR, UV-vis, mass, H-1 NMR, and C-13 NMR together with elemental analysis. (C) 2016 Elsevier B.V. All rights reserved.