Tetrasubstituted Phthalocyanines with Benzoic Acids Moieties

Phthalonitriles substituted with o-hydroxybenzoic, o-aminobenzoic, and o-mercaptobenzoic acids moieties were synthesized by nucleophilic substitution of bromine in 4-bromophthalonitrile and of nitro group in 4-nitrophthalonitrile. Template condensation of these phthalonitriles with metal acetates gave the corresponding phthalocyanines. Metal-free phthalocyanines were synthesized by dissociation of the magnesium complexes of the substituted phthalocyanines in a sulfuric acid medium. Treatment of the resultant phthalocyanines with sodium ethoxide in ethanol yielded sodium salts of the carboxylic acids. The spectral properties of the compounds synthesized were examined.