Synthesis and some properties of 4-{4-[tris(4- octyloxyphenyl)methyl]phenoxy}phthalonitrile and copper, nickel, and cobalt phthalocyaninates on its basis

Abstract

In four stages, by o -alkylation of phenol with 1-bromooctane, alkylation of octyloxybenzene with carbon tetrachloride, alkylation of phenol with tris(4-octyloxyphenyl)methanol, and nucleophilic substitution of the nitro group in 4-nitrophthalonitrile with tris(4-octyloxyphenyl)- 4-hydroxyphenylmethane, 4-{4-[tris(4-octyloxyphenyl)methyl]phenoxy}phthalonitrile was synthesized. Its reactions with copper(II), nickel(II), and cobalt(II) acetates in the presence of urea gave the corresponding metal phthalocyanines. The spectral properties of the obtained compounds were studied. All the phthalocyanines are not associated in chloroform at concentrations up to ~4×10-5 mol/L. They do not exhibit mesomorphic properties, but upon cooling after heating, the copper and nickel complexes pass into a glass state.