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).

Graphical abstractTriplet quantum yields of the newly synthesized metal tetra(1,1′-bi-binaphtoxy)phthalocyanines 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).Figure optionsDownload full-size imageDownload as PowerPoint slide