Synthesis and Photophysical Properties of Annulated Dinuclear and Trinuclear Phthalocyanines

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Abstract
Metal-free mononuclear, dinuclear and trinuclear phthalocyanines were prepared by a mixed cyclotetramerisation of a 1,2,4,5-tetracyanobenzene derivative and 4,5-bis(2,6-dimethylphenoxy)phthalonitrile. For the first time, a π-electron-conjugated trinuclear phthalocyanine was synthesised with phthalocyanine units connected by common annulated benzene rings. The Q band of the trinuclear compound in solution occurs at λ=944 nm whereas those of the dinuclear and mononuclear compounds are at λ=853/830 and 701/664 nm, respectively. Fluorescence quantum yields, fluorescence lifetimes and singlet-oxygen quantum yields of the compounds were determined.