The photophysical properties of menthyl anthranilate: a UV-A sunscreen.
The results of a comprehensive investigation of the photophysical properties of the sunscreen agent menthyl anthranilate in various solvent systems are reported. Luminescence studies reveal that this ester is highly fluorescent (phi f = 0.64 +/- 0.06 in ethanol) and has a solvent-dependent emission maximum in the range of 390-405 nm. Phosphorescence has also been detected in low-temperature glasses with an emission maximum at 445 nm and a lifetime of 2.5 s. Kinetic UV-visible absorption measurements revealed a transient species with absorption maxima at 480 nm and solvent-dependent lifetimes of 26-200 microseconds that are attributed to the triplet state. The triplet state is efficiently quenched by oxygen, leading to the formation of singlet oxygen in all of the solvent systems studied. The singlet-oxygen quantum yields (phi delta) determined by time-resolved near-infrared luminescence measurements were determined to be in the range 0.09-0.12 for all systems.
Department of Chemistry, University of Durham, UK. andrew.beeby@durham.ac.uk
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D006801:Humans; D066298:In Vitro Techniques; D010100:Oxygen / Q000737:chemistry; D010777:Photochemistry; D026082:Singlet Oxygen; D012997:Solvents; D013056:Spectrophotometry, Ultraviolet; D013473:Sunscreening Agents / Q000737:chemistry* / Q000528:radiation effects*; D014466:Ultraviolet Rays; D062367:ortho-Aminobenzoates / Q000737:chemistry* / Q000528:radiation effects*
D012997:Solvents; D013473:Sunscreening Agents; D062367:ortho-Aminobenzoates; D026082:Singlet Oxygen; C413549:menthyl anthranilate; D010100:Oxygen