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Issue 2, 2013
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Excited states of menthyl anthranilate: a UV-A absorber

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Abstract

The photophysical properties of menthyl anthranilate (MA), a UV-A absorber, have been studied through measurements of UV absorption, fluorescence, triplet–triplet absorption and time-resolved thermal lens in ethanol at room temperature and/or 77 K. The phosphorescence and time-resolved electron paramagnetic resonance spectra have also been observed in ethanol at 77 K. The energy levels of the lowest excited singlet (S1) state and triplet (T1) state were determined. The quantum yields of fluorescence, phosphorescence and S1 → T1 intersystem crossing (ISC) were also determined. From the data on the lifetime and quantum yield, the rate constants of the radiative decay, internal conversion and ISC of the excited states of MA were determined. The exceptionally high ISC quantum yield of MA shows that the deactivation processes of the S1 state of MA are different from those of most UV absorbers such as cinnamate, salicylate, 2-hydroxybenzophenone, benzotriazole and dibenzoylmethane derivatives, where the internal conversion rates of the S1 states are much faster than the ISC rates. The observed T1 lifetime and zero-field splitting parameters suggest that the T1 state of MA possesses almost pure 3ππ* character.

Graphical abstract: Excited states of menthyl anthranilate: a UV-A absorber

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Article information


Submitted
15 Jun 2012
Accepted
20 Aug 2012
First published
21 Aug 2012

Photochem. Photobiol. Sci., 2013,12, 246-253
Article type
Paper

Excited states of menthyl anthranilate: a UV-A absorber

A. Kikuchi, K. Shibata, R. Kumasaka and M. Yagi, Photochem. Photobiol. Sci., 2013, 12, 246
DOI: 10.1039/C2PP25190F

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