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

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, H-1 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 degrees 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. (C) 2011 Elsevier B.V. All rights reserved.