A Novel Method for the Peripheral Modification of Phthalocyanines. Synthesis and Third-Order Nonlinear Optical Absorption of β-Tetrakis(2,3,4,5,6-pentaphenylbenzene)phthalocyanine

The title compound, β-tetrakis(2,3,4,5,6-pentaphenylbenzene) phthalocyanine, was prepared by cyclotetramerization of 4-(2,3,4,5,6-pentaphenylbenzene)phthalonitrile, in the presence of hydroquinone. The phthalonitrile derivative was synthesized by a Diels−Alder reaction between 4-(phenylethynyl)phthalonitrile and tetracyclone. This methodology was also extended to alkoxy (butyloxy and dodecyloxy)-substituted polyphenylated phthalocyanines and metallophthalocyanines. The polyphenylated design renders the Pcs soluble in common organic solvents. degenerate four-wave mixing studies of the phthalocyanine in dioxane gave χ(3) = 0.52 × 10-10 esu and 〈γ〉 = 6.12 × 10-32 esu, measured at 1064 nm.