Synthesis of ladder-type oligomers incorporating phthalocyanine units

The condensation of substituted diiminoisoindolines with alkyl-substituted 1,3,3-trichloroisoindolines results in the formation of the highly soluble metal-free phthalocyanines 9, 15, By the same methodology, metal-containing phthalocyanines such as 16, 18 are accessible from suitable metal salts, T he precursors 24 and 26 were obtained from the phthalocyanine 9 and tetracy clone. The generation of the phthalocyanines 23 and 25 possessing isobenzof uran moieties as diene subunits was accomplished; in the presence of excess 28, the tetracyclone-bisadducts 22 and 24 were transformed into the model compounds 29 and 30, while an excess of 20 or 9 leads to the appropriate tr imeroligomers 31 and 32.