Octaarylethylynyl and Octaarylbutadiynyl Phthalocyanines

4,5-Diphenylethynylphthalonitrile, 4,5-di(p-tert-butylphenylethynyl)phthalonitrile, 4,5-di(p-neopentoxyphenylethynyl)phthalonitrile, and 4,5-di(p-neopentoxyphenyl-1,3-butadiynyl)phthalonitrile were prepared via 4,5-diiodophthalonitrile and the appropriate alkyne in palladium-catalyzed coupling reactions. Condensation of the above alkynylphthalonitriles with lithium 1-octanolate in 1-octanol afforded the desired polyalkynylphthalocyanines, but only 2,3,9,10,16,17,22,23-octa (p-neopentoxyphenylethynyl)phthalocyanine and 2,3,9,10,16,17, 22,23-octa (p-neopentoxyphenylbutadnyl)phthalocyanine were soluble enough to be suitably characterized.