Synthesis of non-peripherally substituted tetra(dihexylmalonate) alcohol soluble phthalocyanines

Abstract

Dimethyl-(2,3-dicyanophenyl)malonate was prepared by the reaction of dimethylmalonate and 3-nitrophthalonitrile. A cyclotetramerization reaction of dimethyl-(2,3-dicyanophenyl)malonate with the corresponding divalent metal salt was achieved in hexanol in the presence of DBU, affording the non-peripherally substituted tetra(dihexylmalonate) Cu(II), Pd(II), and Co(II) phthalocyanines. Transesterification occurred under these reaction conditions, so that methyls in the phthalonitrile derivative were converted into hexyl groups during phthalocyanine formation in hexanol. The new compounds were characterized by elemental analyses, FT-IR, H-1-NMR, C-13-NMR, UV-Vis, and mass spectral data.