Synthesis and characterization of novel polyfluorinated porphyrazines

By cyclotetramerization of 2,3-bis(2,3,4,5,6-pentafluorobenzylthio)maleonitrile in the presence of magnesium butanolate, magnesium porphyrazinate carrying eight (2,3,4,5,6-pentafluorobenzylthio) functional groups on the periphery positions has been synthesized. Conversion of the magnesium porphyrazinate into the metal-free derivative was achieved by treatment with trifluoroacetic acid. Further reaction of this product with copper(II) acetate, zinc(II) acetate and cobalt(II) acetate have led to the metallo derivatives [M = Cu(II), Zn(II), Co(II)]. These novel complexes were characterized by elemental analysis, together with FT-IR, 1H NMR, 13C NMR, 19F NMR, UV–vis, and mass spectral data.

Synthesis and characterization of a new (2,3,4,5,6-pentafluorobenzylthio) ligand and its metal free, Mg(II), Cu(II), Zn(II) and Co(II) porphyrazine complexes have been described. These novel 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 slideHighlights
► New polyfluorinated porphyrazine molecules are synthesized.
► Solubility of metallo porphyrazines in common solvents is enhanced.
► No new Q band absorptions are observed in the aggregation study.
► The presence of an electron donating group causes a bathochromic shift on Q bands.