Chromenone 12-crown-4 substituted zinc phthalocyanine complexes: Investigation of spectral, photophysical and photochemical properties

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2011-10, Vol.81 (1), p.690-697
• Main Authors: Esenpınar, Aliye Aslı, Durmuş, Mahmut, Bulut, Mustafa
• Format: Article
• Language: English
• Subjects: Coumarin ( 2H-chromen-2-one); Crown ether; Fluorescence; Phthalocyanine; Quantum yield; Singlet oxygen
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2011.07.003

The synthesis of novel 6,7-[(12-crown-4)-3-[ p-(3,4-dicyanophenoxy)phenyl]coumarin ( 1), 6,7-[(12-crown-4)-3-[ p-(2,3-dicyanophenoxy)phenyl]coumarin ( 2), and their corresponding tetra-(chromenone 12-crown-4)-substituted zinc (II) phthalocyanine complexes ( 3 and 4) have been prepared. These new compounds have been characterized by elementel analysis, 1H NMR ( 1 and 2), MALDI-TOF, IR and UV–Vis spectral data. The fluorescence intensity changes for 1 and 2 by addition of Na + or K + ions have been determined at 25 °C in THF. Intensity of the binding Na +- and K +-complexes ( 1 and 2) have decreased. The effects of the chromenone crown ether on the phthalocyanine molecule concerning photophysical and photochemical properties are also investigated. Photodegredation, singlet oxygen, fluorescence quantum yields, and fluorescence lifetimes of zinc phthalocyanine complexes ( 3 and 4) are also examined in DMSO. [Display omitted] ► Synthesis of chromenone crown ether substituted zinc phthalocyanine complexes. ► Photophysical and photochemical properties in DMSO solution. ► New fluorescence sensor. ► Photodynamic therapy. The synthesis of novel 6,7-[(12-crown-4)-3-[ p-(3,4-dicyanophenoxy)phenyl]coumarin ( 1), 6,7-[(12-crown-4)-3-[ p-(2,3-dicyanophenoxy)phenyl]coumarin ( 2), and their corresponding tetra-(chromenone 12-crown-4)-substituted zinc (II) phthalocyanine complexes ( 3 and 4) have been prepared. These new compounds have been characterized by elementel analysis, 1H NMR ( 1 and 2), MALDI-TOF, IR and UV–Vis spectral data. The fluorescence intensity changes for 1 and 2 by addition of Na + or K + ions have been determined at 25 °C in THF. Intensity of the binding Na +- and K +-complexes ( 1 and 2) have decreased. The effects of the chromenone crown ether on the phthalocyanine molecule concerning photophysical and photochemical properties are also investigated. Photodegredation, singlet oxygen, fluorescence quantum yields, and fluorescence lifetimes of zinc phthalocyanine complexes ( 3 and 4) are also examined in DMSO.