Synthesis and characterization of new soluble fluorinated seco-porphyrazines

Magnesium porphyrazinate substituted with eight 3,5-bis(trifluoromethyl)phenyl groups on the peripheral positions has been synthesized by the cyclotetramerization of 3,4-[3,5-bis(trifluoromethyl)phenyl]pyrroline-2,5-diimine in the presence of magnesium butanolate. Acid-mediated demetallation of the magnesium porphyrazine resulted in peripheral oxidation of one pyrrole ring to reveal the seco-porphyrazine, octakis[3,5-bis(trifluoromethyl)phenyl]-2-seco-porphyrazine-2,3-dione. Further reaction of this product with copper (II) acetate, zinc (II) acetate and cobalt (II) acetate has led to the metallo-derivatives, {octakis[3,5-bis(trifluoromethyl)phenyl]-2-seco-2,3-dioxoporphyrazinato} M(II) [M = Cu(II), Zn(II), Co(II)]. These new soluble complexes were characterized by elemental analysis, together with FT-IR, 1H NMR, 13C NMR, 19F NMR, UV–Vis and mass spectral data.

Novel soluble seco-porphyrazine type partially oxidized derivatives surrounded by eight 3,5-bis(trifluoromethyl)phenyl-appending groups have been synthesized. These complexes were characterized by elemental analysis, together with FT-IR, 1H NMR, 13C NMR, 19F NMR, UV–Vis and mass spectral data.Figure optionsDownload as PowerPoint slideResearch highlights
► Fluorinated metallo tetrapyrrol compounds like porphyrazines form a class of coordination compounds which have currently been receiving a great deal of attention due to their interesting electron transport characteristics. Also, fluorocarbons display enhanced hydrophobicity, chemical resistance, thermal stability and lipophobicity in comparison to their hydrocarbon counterparts. Therefore, the products can be candidates to use in these areas.