Synthesis and Characterization of Several Soluble Tetraphenoxy-Substituted Copper and Zinc Phthalocyanines

Abstract

Synthesis of copper and zinc phthalocyanines (Pcs) bearing phenoxy-substituents is described. Precursors required for the preparation of Pcs 9-16 are prepared by a nucleophilic aromatic substitution reaction between a sterically hindered phenol derivative and 4-nitrophthalonitrile (1) or 3-nitrophthalonitrile (2). Cyclotetramerization of the resulting precursor phthalonitriles in DMAE or in pentan-1-ol catalyzed by DBU gives desired Pcs, which are well soluble in common organic solvents, such as chloroform and dichloromethane. Each of these Pcs are composed of four constitutional isomers and are characterized by ¹H NMR, UV/Vis, IR and mass spectra, as well as elemental analysis, which are consistent with the proposed structures.

Key words

phthalocyanines - zinc - copper - synthesis - phenols

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