Synthesis and characterization of new soluble polyfluorinated seco-porphyrazines

The synthesis of new polyfluorinated magnesium porphyrazine bearing pentafluorophenyl moieties was achieved by cyclotetramerization of 3,4-bis(pentafluorophenyl)pyrroline-2,5-diimine in the presence of Mg(BuO)(2). Acid-mediated demetallation of the magnesium porphyrazine resulted in peripheral oxidation of one pyrrole ring to reveal the seco-porphyrazine, [2,3,7,8,12,13,17,18-octakis(pentafluorophenyl)-2-seco-2,3-dioxoporphyrazine]. Further reaction of that product with copper (II) acetate, zinc (II) acetate and cobalt (II) acetate has led to the metallated seco-derivatives, [2,3,7,8,12,13,17,18-octakis(pentafluorophenyl)-2-seco-2,3-dioxoporphyrazinato] M(II) [M = Cu(II), Zn(II), Co(II)]. The spectroscopic and aggregation behavior of all the target porphyrazines were investigated in different solvents and at different concentrations in chloroform. The compounds were characterized by using many spectroscopic techniques such as FT-IR, H-1 NMR, C-13 NMR, F-19 NMR. UV-vis, mass and elemental analysis. The porphyrazines were soluble in various organic solvents such as chloroform, dichloromethane, pyridine, and THF. (C) 2012 Elsevier B.V. All rights reserved.