Synthesis and characterisation of some 1,4,8,11,15,18,22,25-octa-alkyl- and 1,4,8,11,15,18-hexa-alkyl-22,25-bis(carboxypropyl)phthalocyanines

Abstract

A series of 3,6-dialkylphthalonitriles and 3,6-bis(4,4,4-trimethoxybutyl) phthalonitrile have been prepared via Diels–Alder reactions of 2,5-disubstituted furans or thiophene 1,1-dioxides with fumaro-nitrile. The phthalonitriles were converted into the title phthalocyanines as metal-free and copper(II) derivatives. The macrocycles were characterised using ¹H NMR and optical spectroscopy, and fast-atom bombardment mass spectrometry. Certain examples exhibit discotic liquid crystal behaviour.