Synthesis and characterization of soluble porphyrazines bearing octakis 2-anthraquinonylmethylthio substituents

By cyclotetramerization of 1,2-bis(2-anthraquinonylmethylthio)maleonitrile in the presence of magnesium butanolate, magnesium porphyrazinate carrying eight (2-anthraquinonylmethylthio) functional groups on peripheral positions has been synthesized. The metal-free derivative was obtained by treatment with trifluoroacetic acid; reaction of this product with copper(II) acetate, zinc(II) acetate, and cobalt(II) acetate led to the metal porphyrazinates [M = Cu(II), Zn(II), and Co(II)]. These new compounds have been characterized by elemental analysis, together with FT-IR, H-1-NMR, C-13-NMR, UV-Vis, and mass spectral data.