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Photochemistry of aqueous solutions of kynurenic acid and kynurenine yellow

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Abstract

The photophysics and photochemistry of kynurenic acid (KNA) and kynurenine yellow (KNY) in neutral aqueous solutions were investigated using time-resolved optical spectroscopy. Both molecules have similar quinoline-like structures, the only difference being the absence of conjugation in the nitrogen containing cycle in KNY. The main channel of S1 excited state decay in the case of partially-unconjugated KNY is the solvent assisted S1 → S0 radiationless transition via intermolecular hydrogen bonds (ΦIC = 0.96), whereas, in the case of fully-conjugated KNA, it is intersystem crossing to the triplet state (ΦT = 0.82). The major intermediate products of the singlet excited KNY deactivation are the triplet state (ΦT = 0.022) and, most probably, the enol form (Φenol = 0.012), which decay with the formation of 2,3-dihydro-4-hydroxyquinoline and 4-hydroxyquinoline, respectively. The results obtained show that KNA and KNY, which are products of the decomposition of the UV filter kynurenine, are significantly more photoactive and less photostable than the parent molecule.

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Authors and Affiliations

  1. International Tomography Center SB RAS, Institutskaya str., 3A, 630090, Novosibirsk, Russia

    Ekaterina A. Zelentsova, Peter S. Sherin, Olga A. Snytnikova & Yuri P. Tsentalovich

  2. Novosibirsk State University, Pirogova str. 2, 630090, Novosibirsk, Russia

    Ekaterina A. Zelentsova, Olga A. Snytnikova, Robert Kaptein & Yuri P. Tsentalovich

  3. Department of Physical Chemistry, University of Geneva, quai Ernest-Ansermet 30, CH-1211, Geneva, Switzerland

    Peter S. Sherin & Eric Vauthey

  4. Bijvoet Center, Utrecht University, Utrecht, The Netherlands

    Robert Kaptein

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  1. Ekaterina A. Zelentsova
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Correspondence to Yuri P. Tsentalovich.

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† Electronic supplementary information (ESI) available. See DOI: 10.1039/c2pp25357g

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Zelentsova, E.A., Sherin, P.S., Snytnikova, O.A. et al. Photochemistry of aqueous solutions of kynurenic acid and kynurenine yellow. Photochem Photobiol Sci 12, 546–558 (2013). https://doi.org/10.1039/c2pp25357g

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