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Role of Solvent, pH, and Molecular Size in Excited-State Deactivation of Key Eumelanin Building Blocks: Implications for Melanin Pigment Photostability

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    Role of Solvent, pH, and Molecular Size in Excited-State Deactivation of Key Eumelanin Building Blocks: Implications for Melanin Pigment Photostability
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    Department of Chemical Physics, Lund University, Box 124, S 22100 Lund, Sweden, Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Naples, Italy, Department of Physics and Nanotechnology, Aalborg University, Denmark, and Biophysics Group, Department of Physics and Astronomy, Faculty of Sciences, Vrije Universiteit, De Boelelaan 1081, 1081 HV Amsterdam
    [email protected]
    †Lund University.
    ‡University of Naples Federico II.
    §Aalborg University.
    ∥Vrije Universiteit.
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    Cite this: J. Am. Chem. Soc. 2008, 130, 50, 17038–17043
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    https://doi.org/10.1021/ja806345q
    Published November 13, 2008
    Copyright © 2008 American Chemical Society
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    Ultrafast time-resolved fluorescence spectroscopy has been used to investigate the excited-state dynamics of the basic eumelanin building block 5,6-dihydroxyindole-2-carboxylic acid (DHICA), its acetylated, methylated, and carboxylic ester derivatives, and two oligomers, a dimer and a trimer in the O-acetylated forms. The results show that (1) excited-state decays are faster for the trimer relative to the monomer; (2) for parent DHICA, excited-state lifetimes are much shorter in aqueous acidic medium (380 ps) as compared to organic solvent (acetonitrile, 2.6 ns); and (3) variation of fluorescence spectra and excited-state dynamics can be understood as a result of excited-state intramolecular proton transfer (ESIPT). The dependence on the DHICA oligomer size of the excited-state deactivation and its ESIPT mechanism provides important insight into the photostability and the photoprotective function of eumelanin. Mechanistic analogies with the corresponding processes in DNA and other biomolecules are recognized.

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    Cite this: J. Am. Chem. Soc. 2008, 130, 50, 17038–17043
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    Published November 13, 2008
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