Synthesis and Properties of 4-{4-[Tris(4-octyloxyphenyl)methyl]phenoxy}phthalonitrile and Copper, Nickel, and Cobalt Phthalocyaninates on Its Basis

For the synthesis of 4-{4-[tris(4-octyloxyphenyl)methyl]phenoxy}phthalonitrile, a method was proposed which involves 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 for the residue of tris-(4-octyloxyphenyl)-4-hydroxyphenylmethane. By the reactions of the resulting phthalonitrile with copper(II), nickel(II), and cobalt(II) acetates in the presence of urea, corresponding metal phthalocyanines were obtained. The spectral properties of the resulting compounds were studied. These phthalocyanines are not associated in chloroform at concentrations up to ~ 4×10 –5 M. They do not show mesomorphic properties, but the copper and nickel complexes pass into vitrified state upon cooling after heating.