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Complexes of tetrabenzo[5,10,15,20]tetraazaporphyrins, known as phthalocyanines, are an important class of macrocyclic compounds, which due to their unique properties have found a wide range of applications. The close analogs of phthalocyanines are tetrabenzotriazaporphyrins, in which one of the meso-nitrogen atoms is substituted by a carbon atom. Tetrabenzo[5,10,15]triazaporphyrins are suggested as photoconducting materials,[1] fluorescent markers in medicine,[2,3] and gas sensors.[4] These compounds remain much less synthetically available than phthalocyanines. The first report on the synthesis of tetrabenzo[5,10,15] triazaporphyrin by heating of the mixture of phthalonitrile, 3-methylenephthalimide and copper chloride at 250°C was published in 1938.[5] One of the common methods of synthesis of tetrabenzo[5,10,15]triazaporphyrins, used up to now, is the interaction of phthalonitrile with organomagnesium reagents with following refluxing in highly boiling solvent.[6,7] There is only one communication on the template synthesis of zinc complex of 20-phenyltetrabenzo[5,10,15]triazaporphyrin on the basis of interaction of 1,3-diiminoisoindoline with phenylacetic acid in the presence of template agent (zinc oxide).[8] Here, we propose a new synthetic method for zinc complexes of 20-aryltetrabenzo[5,10,15]triazaporphyrins by the reaction of unsubstituted phthalodinitrile with quaternary salts of triphenylphosphonium in the presence of zinc powder at gradual heating from 200 to 300oC.§

New Synthetic Method for Zinc Complexes of 20-Aryltetrabenzo[5,10,15]-triazaporphyrin