Synthesis and properties of phthalocyanine zinc(II) complexes replaced with oxygen and sulfur linked adamantane moieties

Novel, zinc (II) phthalocyanines substituted with 2-adamantanol and 1-adamantanethiol moieties were prepared from the corresponding phthalonitriles employing commercially available 3- and 4-nitrophthalonitrile as the starting material. The Q-band of tetra-α-substituted phthalocyanines occurred at longer wavelengths than those of the corresponding, tetra-β-substituted phthalocyanines. Substituents at the β position increased ΦF values; all phthalocyanines studied displayed excellent singlet oxygen generations ability, with α-substituted dyes showing higher ΦΔ values than their β-isomers. The dyes exhibited good photo-stability, with α-substituted phthalocyanines proving to be of higher stability than the corresponding β-isomers.