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

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-butylphthalodinitrite 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. Copyright (C) 2003 Society of Porphyrins & Phthalocyanines.