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Absorption and Emission of the Apigenin and Luteolin Flavonoids: A TDDFT Investigation

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    Absorption and Emission of the Apigenin and Luteolin Flavonoids: A TDDFT Investigation†
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    Dipartimento di Chimica, Università degli Studi di Perugia, via Elce di Sotto 8, I-06123 Perugia, Italy and Istituto di Scienze e Tecnologie Molecolari del CNR (CNR-ISTM), c/o Dipartimento di Chimica, via Elce di Sotto 8, I-06123 Perugia, Italy
    †Part of the “Vincenzo Aquilanti Festschrift”.
    * Corresponding author. E-mail: [email protected]
    ‡Università degli Studi di Perugia.
    §Istituto di Scienze e Tecnologie Molecolari del CNR (ISTM-CNR).
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2009, 113, 52, 15118–15126
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    https://doi.org/10.1021/jp9052538
    Published September 1, 2009
    Copyright © 2009 American Chemical Society
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    Abstract

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    The absorption and emission properties of the two components of the yellow color extracted from weld (Reseda luteola L.), apigenin and luteolin, have been extensively investigated by means of DFT and TDDFT calculations. Our calculations reproduce the absorption spectra of both flavonoids in good agreement with the experimental data and allow us to assign the transitions giving rise to the main spectral features. For apigenin, we have also computed the electronic spectrum of the monodeprotonated species, providing a rationale for the red-shift of the experimental spectrum with increasing pH. The fluorescence emission of both apigenin and luteolin has then been investigated. Excited-state TDDFT geometry optimizations have highlighted an excited-state intramolecular proton transfer (ESIPT) from the 5-hydroxyl to the 4-carbonyl oxygen of the substituted benzopyrone moiety. By computing the potential energy curves at the ground and excited states as a function of an approximate proton transfer coordinate for apigenin, we have been able to trace an ESIPT pathway and thus explain the double emission observed experimentally.

    Copyright © 2009 American Chemical Society

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    Supporting Information

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    Apigenin computed spectra at different levels of calculation; apigenin S0 main geometrical parameters at different levels of calculation; apigenin frontier MO energies computed in water and methanol solution; apigenin computed transitions, oscillator strengths, and composition in methanol solution; apigenin dipole moments for S0, S1, and S2 computed in water and in vacuo; apigenin transition dipole moments for S0 → S1, S0 → S2, and S0 → S3 excitations computed in water and in vacuo; computed contributions to ΔGs for the pKa calculations of monodeprotonated apigenin in position 7, 4′, and 5; monodeproptonated apigenin spectra computed at different levels of calculation; monodeprotonated apigenin frontier molecular orbital energies and isodensity plots for clusters with zero, one, three, and five explicit water molecules; and monodeprotonated apigenin computed absorption spectra for clusters with zero, one, three, and five water molecules. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Phys. Chem. A 2009, 113, 52, 15118–15126
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    https://doi.org/10.1021/jp9052538
    Published September 1, 2009
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