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Metal-free copper and cobalt(II) binuclear phthalocyanines, in which the two phthalocyanine nuclci are covalently linked through five-atom bridges, have been prepared and characterized. Some new metal-free, copper, cobalt(II), and zinc 2,9,16,23-tetraalkoxyphthalocyanines, some of which are extremely soluble in organic solvents, are described.

. J. Chem. 63, 3057 (1985).Binuclear phthalocyanines in which the two phthalocyanine nuclei are covalently linked through four-atom bridges, derived from catechol, have been prepared and characterized. Metal-free 2,9,16,23-tetra-(3,3-dimethylbutyl)phthalocyanine and 2,9,16,23-tetra-(2-trimethylsilylethyl)phthalocyanine were prepared as examples of non-oxygenated mononuclear phthalocyanines soluble in organic solvents. Catalytic hydrogenation of 1,2-bis-(3,4-dicyanopheny1)ethyne and 1,4-bis-(3,4-dicyanophenyl)buta-l,3-diyne gave 1,2-bis- (3,4-dicyanopheny1)ethane and 1,4-bis-(3,4-dicyanopheny1)butane respectively. From these precursors, metal-free phthalocyanine dimers containing ethylene and tetramethylene bridges, joining the phthalocyanine nuclei, were prepared. Two of the two-atom bridge phthalocyanine dimers represent the first characterized phthalocyanine dimers not containing alkoxy or oxygenated groups.

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