Non-aggregating phthalocyanines with bulky 2,4-di-tert-butylphenoxy-substituents

In this paper, a bulky (2,4-di-tert-butylphenoxy)-substituted phthalonitrile was synthesized by nucleophilic displacement of nitro group in 4-nitro-phthalonitrile with 2,4-di-tert-butylphenol. Its cyclotetramerization in the presence of zinc(II), cobalt(II), nickel(II) or copper(II) ion with catalytic amount of DBU resulted in phthalocyanines being extensively soluble in number of organic solvents. Aggregation did not occur even in concentrations up to 1 × 10−3 M. The new compounds were characterized by elemental analyses, UV–vis, IR and NMR spectra.