Synthesis of 1,2-bis(3,4-dicyanophenoxymethyl)benzene and binuclear zinc phthalocyanines of clamshell and ball types

Abstract

A novel 1,2-bis(3,4-dicyanophenoxymethyl)benzene was synthesized from 1,2-bis-(hydroxymethyl)benzene and 4-nitrophthalodinitrile. Its condensation with 4-tert-butylphthalodinitrile results in a binuclear phthalocyanine of clamshell type. Reaction of bisphthalodinitrile with a large excess of zinc acetate gives rise to a binuclear phthalocyanine of ball type (33% yield). The successful syntheses of these binuclear phthalocyanines were carried out by microwave irradiation and solid phase methods.