Synthesis and spectral properties of novel seco-porphyrazines with eight 4-biphenyl groups

Magnesium porphyrazinate substituted with eight 4-biphenyl groups on the periphery positions has been synthesized for the first time from cyclotetramerization of 1,2-bis(4-biphenyl)maleonitrile in the presence of magnesium butanolate. Its demetalation by treatment with trifluoroacetic acid, resulted in a partially oxidized product, namely, octakis(4-biphenyl)-2-seco-porphyrazine-2,3-dione. Further reaction of this product with copper(II) acetate, zinc(11) acetate and cobalt(II) acetate has led to the metallo derivatives, [octakis(4-biphenyl)-2-seco-2,3-dioxoporphyrazinato] M(II) (M = Cu, Zn, Co). These novel compounds have been characterized by elemental analysis, together with FT-IR,(1)H NMR, UV-Vis and mass spectral data. (C) 2008 Elsevier Ltd. All rights reserved.