Xanthone-photosensitized detoxification of the veterinary anthelmintic fenbendazole
•Photocatalyzed oxidation of fenbendazole by aromatic ketones under solar-simulated steady-state irradiation.•Characterization of the transients generated by laser flash photolysis (LFP).•Detoxification of fenbendazole solutions revealed by the inhibition of mobility in the Daphnia magna assay.
Fenbendazole (1) is a common veterinary anthelmintic, toxic to water living microorganisms. Fluorescence quantum yields of 1 were found to be 0.11 in acetonitrile, 0.068 in methanol, 0.034 in cyclohexane, and 0.013 in water. The singlet excited state energy was ca. 96 kcal mol−1 in all solvents. The phosphorescence spectrum of 1 in ethanol at 77 K displayed a maximum at 450 nm, leading to a triplet energy of 75 kcal mol−1. Experimental excited state energies agree well with the results of DFT calculations at the time-dependent B3LYP/6-311+G(d,p)//B3LYP/6-31G(d) level. Laser flash photolysis (LFP) of 1 at 266 nm led to transients absorbing in the 300–700 nm range, ascribed to radical cation 1+, which were also observed upon 355 nm LFP of xanthone (XA) in the presence of 1. Solar-simulated photolysis revealed XA-enhanced photodegradation of 1 and led to decreased toxicity, as shown by Daphnia magna assays.
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Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 264, 15 July 2013, Pages 34–40