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

A. Corani, A. Pezzella, T. Passcher, T. Gustavsson, D. Markovitsi, Jannetje Maria Huijser, M. D'Ischia, V. Sundström

Research output: Contribution to journalArticleAcademicpeer-review

24 Citations (Scopus)

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 × 108 s
Original languageEnglish
Pages (from-to)1383-1388
Number of pages6
JournalJournal of physical chemistry letters
Volume4
Issue number9
DOIs
Publication statusPublished - 2013

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Proton transfer
Carboxylic Acids
Carboxylic acids
Excited states
carboxylic acids
protons
excitation
Fluorescence spectroscopy
pigments
Pigments
time constant
Anions
Methanol
Rate constants
Energy dissipation
Skin
Negative ions
methyl alcohol
energy dissipation
anions

Keywords

  • METIS-295650
  • IR-85481

Cite this

Corani, A., Pezzella, A., Passcher, T., Gustavsson, T., Markovitsi, D., Huijser, J. M., ... Sundström, V. (2013). Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds. Journal of physical chemistry letters, 4(9), 1383-1388. https://doi.org/10.1021/jz400437q
Corani, A. ; Pezzella, A. ; Passcher, T. ; Gustavsson, T. ; Markovitsi, D. ; Huijser, Jannetje Maria ; D'Ischia, M. ; Sundström, V. / Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds. In: Journal of physical chemistry letters. 2013 ; Vol. 4, No. 9. pp. 1383-1388.
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Corani, A, Pezzella, A, Passcher, T, Gustavsson, T, Markovitsi, D, Huijser, JM, D'Ischia, M & Sundström, V 2013, 'Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds' Journal of physical chemistry letters, vol. 4, no. 9, pp. 1383-1388. https://doi.org/10.1021/jz400437q

Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds. / Corani, A.; Pezzella, A.; Passcher, T.; Gustavsson, T.; Markovitsi, D.; Huijser, Jannetje Maria; D'Ischia, M.; Sundström, V.

In: Journal of physical chemistry letters, Vol. 4, No. 9, 2013, p. 1383-1388.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Excited-State Proton-Transfer Processes of DHICA Resolved: From Sub-Picoseconds to Nanoseconds

AU - Corani, A.

AU - Pezzella, A.

AU - Passcher, T.

AU - Gustavsson, T.

AU - Markovitsi, D.

AU - Huijser, Jannetje Maria

AU - D'Ischia, M.

AU - Sundström, V.

PY - 2013

Y1 - 2013

N2 - 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 × 108 s

AB - 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 × 108 s

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KW - IR-85481

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