Syntheses of Monometalated and Unsymmetrically Substituted Binuclear Phthalocyanines and a Pentanuclear Phthalocyanine by Solution and Polymer Support Methods

Article abstract of DOI:10.1021/jo00001a019

Binuclear phthalocyanines in which two different phthalocyanine nuclei are covalently linked through five-atom bridges, derived from 2-ethyl-2-methylpropane-1,3-diol, are prepared.In the examples, one phthalocyanine ring is always substituted with neopentyloxy substitutents, while the other phthalocyanine rin is unsubstituted or contains tert-butyl substituents or a neopentoxy-substituted copper phthalocyanine, constituting a binuclear phthalocyanine in which only one ring is metalated.The precursor, 2-(2-hydroxymethyl)-2-methylbutoxy)-9,16,23-trineopentoxyphthalocyanine was prepared in solution and also by solid-phase methods, using polymer-bound trityl chloride derived from a 1percent divinylbenzene-co-styrene copolymer.In some experiments some rare examples of demetalation of some zinc phthalocyanines are noted during phthalocyanine formation.A modified flash chromatography procedure proved to be useful for separating similarly substituted mononuclear phthalocyanines.