Synthesis and photophysical properties of 1,1′-binaphthol substituted phthalocyanines

We report on the synthesis, characterization and photophysical properties of a new symmetrically tetra substituted {at non-peripheral positions with tetra(1,1′-bi-binaphtoxy)} phthalocyanines containing H₂, Mg(II), Al(III)Cl, Si(IV)Cl₂ in the central cavity. The synthesized compounds were characterized by the elemental analyses, UV-Vis, FT-IR and ¹H NMR spectroscopies. The fluorescence quantum yields, triplet quantum yields and lifetimes of the newly synthesized H₂, Mg, Al, and Si phthalocyanines were explored. Triplet quantum yields ranged from 0.24 to 0.54. The triplet lifetime for the silicon phthalocyanine derivative was the highest ever reported for a phthalocyanine (∼3.5 ms).