Synthesis and properties of crown ether functionalized coumarin substituted zinc phthalocyanine

The novel 6,7-[15-crown-5]-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin (1) and its non-peripherally substituted zinc phthalocyanine complex (2) have been prepared and characterized by elemental analysis, 1H NMR (for compound 1), MALDI-TOF, FT-IR and UV–Vis spectral data. Fluorescence intensity changes of compound 1 have been determined by addition of Na+ or K+ ions at 25 °C in THF. The effects of the chromenone crown ether substituent of the phthalocyanine molecule on the photophysical (fluorescence quantum yield and lifetime) and photochemical (singlet oxygen generation and photodegradation) properties were also investigated. The fluorescence of the zinc phthalocyanine complex is effectively quenched by addition of 1,4-benzoquinone (BQ).

The novel 6,7-[15-crown-5]-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin (1) and its non-peripherally zinc phthalocyanine complex (2) have been prepared and characterized. The effects of the chromenone crown ether substituent of the phthalocyanine molecule on the photophysical and photochemical properties were also investigated.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of the novel 6,7-[15-crown-5]-3-[p-(2,3-dicyanophenoxy)phenyl]coumarin and its zinc(II) phthalocyanine complex.
► Photophysical and photochemical properties in DMSO solution.
► Singlet oxygen quantum yield (ΦΔ).
► Photodynamic therapy.