Synthesis of organo-soluble metallophthalocyanines bearing electron-withdrawing substituents

The syntheses of organo-soluble metallophthalocyanines having sulfo- and sulfonamido- electron-withdrawing substituents are reported. The simple cation exchange of the readily available tetrasodium salt of metallo-sulfophthalocyanines 1 (M = Ni, Co, Fe, Cr) by alkylammonium salts afforded the sulfophthalocyanines 2 and 3 in good yields. Complexes 2 featuring two long C18 alkyl chains are only soluble in organic solvents while tetrabutylammonium counter ions exhibit a dual solubility in both organic solvents and water for compounds 3. The tetrasulfonamidophthalocyanine complexes 5–7 with four C8, four C18 or eight C8 alkyl chains have been obtained after chlorination of the sulfophthalocyanines 1 leading to the chlorosulfonyl derivatives 4, followed by reaction with various substituted amines. The synthesis of the chromium precursors with tetrasulfo and tetrachlorosulfonyl substituents is also described. Copyright © 2001 John Wiley & Sons, Ltd.