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Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds

Corani, Alice LU ; Pezzella, Alessandro ; Pascher, Torbjörn LU ; Gustavsson, Thomas ; Markovitsi, Dimitra ; Huijser, Annemarie LU ; d'Ischia, Marco and Sundström, Villy LU (2013) In The Journal of Physical Chemistry Letters 4(9). p.1383-1388
Abstract
Excited-state proton transfer has been hypothesized as a mechanism for UV energy dissipation in eumelanin skin pigments. By using time resolved fluorescence spectroscopy, we show that the previously proposed, but unresolved, excited-state intramolecular proton transfer (ESIPT) of the eumelanin building block 5,6-dihydroxyindole-2-carboxylic acid (DHICA) occurs with a time constant of 300 fs in aqueous solution but completely stops in methanol. The previously disputed excited-state proton transfer involving the 5- or 6-OH groups of the DHICA anion is now found to occur from the 6-OH group to aqueous solvent with a rate constant of 4.0 x 10(8) s(-1).
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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
The Journal of Physical Chemistry Letters
volume
4
issue
9
pages
1383 - 1388
publisher
The American Chemical Society (ACS)
external identifiers
  • wos:000318536500004
  • pmid:26282289
  • scopus:84877118614
  • pmid:26282289
ISSN
1948-7185
DOI
10.1021/jz400437q
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Chemical Physics (S) (011001060)
id
010f77fe-3824-455e-8877-5d5927026c84 (old id 3815335)
date added to LUP
2016-04-01 14:55:22
date last changed
2022-02-12 06:05:28
@article{010f77fe-3824-455e-8877-5d5927026c84,
  abstract     = {{Excited-state proton transfer has been hypothesized as a mechanism for UV energy dissipation in eumelanin skin pigments. By using time resolved fluorescence spectroscopy, we show that the previously proposed, but unresolved, excited-state intramolecular proton transfer (ESIPT) of the eumelanin building block 5,6-dihydroxyindole-2-carboxylic acid (DHICA) occurs with a time constant of 300 fs in aqueous solution but completely stops in methanol. The previously disputed excited-state proton transfer involving the 5- or 6-OH groups of the DHICA anion is now found to occur from the 6-OH group to aqueous solvent with a rate constant of 4.0 x 10(8) s(-1).}},
  author       = {{Corani, Alice and Pezzella, Alessandro and Pascher, Torbjörn and Gustavsson, Thomas and Markovitsi, Dimitra and Huijser, Annemarie and d'Ischia, Marco and Sundström, Villy}},
  issn         = {{1948-7185}},
  language     = {{eng}},
  number       = {{9}},
  pages        = {{1383--1388}},
  publisher    = {{The American Chemical Society (ACS)}},
  series       = {{The Journal of Physical Chemistry Letters}},
  title        = {{Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds}},
  url          = {{http://dx.doi.org/10.1021/jz400437q}},
  doi          = {{10.1021/jz400437q}},
  volume       = {{4}},
  year         = {{2013}},
}