Hexadeca(pyrazol-1-yl)phthalocyanine: A Soluble Phthalocanine Absorbing at 780 nm.
Hexadeca(pyrazol-1-yl)phthalocyanine, a phthalocya-nine bearing in its periphery 16 pyrazole residues has been prepared in two steps from 3,4,5,6-tetrafluoro-1,2-dicyanobenzene in 90% yield. The crystal and molecular structure of 3,4,5,6-tetra(pyrazol-1-yl)-1,2-dicyanobenzene intermediate has been determined: triclinic P-1, a = 11.6632(5), b = 11.2553(7), c = 8.7338(4) , a = 110.893(4), b = 104.709(4), g = 60.608(4), V = 928.86(9) 3, Z = 2, R(F) = 0.037 and Rw(F) = 0.045. The new phthalocyanine is soluble in organic solvents and has an absorption band at 780 nm in ethanol 95. Semiempirical AM1 calculations have been carried on 3,4,5,6-tetrafluoro-1,2-dicyanobenzene and several (pyrrol-1-yl and pyrazol-1-yl)phthalocyanines.