Excited-state proton-transfer processes of DHICA resolved: From sub-picoseconds to nanoseconds

Journal of Physical Chemistry Letters

Volumn 4, Issue 9, 2013, Pages 1383-1388

  Corani, Alice ^a   Pezzella, Alessandro ^b   Pascher, Torbjörn ^a   Gustavsson, Thomas ^c   Markovitsi, Dimitra ^c   Huijser, Annemarie ^a   D'Ischia, Marco ^b   Sundström, Villy ^a  

^a LUND UNIVERSITY   (Sweden)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c DIF   (France)

Author keywords

DHICA; ESPT; eumelanin; solvent; time resolved fluorescence

Indexed keywords

5 ,6-DIHYDROXYINDOLE-2-CARBOXYLIC ACIDS; DHICA; ESPT; EUMELANINS; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; EXCITED-STATE PROTON TRANSFER; TIME-RESOLVED FLUORESCENCE; TIME-RESOLVED FLUORESCENCE SPECTROSCOPY;

ENERGY DISSIPATION; FLUORESCENCE SPECTROSCOPY; MELANIN; PROTON TRANSFER; RATE CONSTANTS; SOLVENTS;

EXCITED STATES;

EID: 84877118614     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz400437q     Document Type: Article

References (37)

1. Prota, G Melanins and Melanogenesis; Academic Press: San Diego, CA, 1992.
2. Panzella, L.; Napolitano, A.; d'Ischia, M. Is DHICA the Key to Dopachrome Tautomerase and Melanocyte Functions? Pigm. Cell Melanoma Res. 2011, 24, 248-249
3. Kovacs, D.; Flori, E.; Maresca, V.; Ottaviani, M.; Aspite, N.; Dell'Anna, M. L.; Panzella, L.; Napolitano, A.; Picardo, M.; d'Ischia, M. The Eumelanin Intermediate 5,6-Dihydroxyindole-2-Carboxylic Acid Is a Messenger in the Cross-Talk among Epidermal Cells J. Invest. Dermatol. 2012, 132, 1196-1205
4. Meredith, P.; Powell, B. J.; Riesz, J.; Nighswander-Rempel, S. P.; Pederson, M. R.; Moore, E. G. Towards Structure-Property-Function Relationships for Eumelanin Soft Matter 2006, 2, 37-44
5. Peles, D. N.; Simon, J. D. Direct Measurement of the Ultraviolet Absorption Coefficient of Single Retinal Melanosomes Photochem. Photobiol. 2010, 86, 279-281
6. Huijser, A.; Pezzella, A.; Hannestad, J. K.; Panzella, L.; Napolitano, A.; d'Ischia, M.; Sundstrom, V. UV-Dissipation Mechanisms in the Eumelanin Building Block DHICA ChemPhysChem 2010, 11, 2424-2431
7. Huijser, A.; Pezzella, A.; Sundstrom, V. Functionality of Epidermal Melanin Pigments: Current Knowledge on UV-Dissipative Mechanisms and Research Perspectives Phys. Chem. Chem. Phys. 2011, 13, 9119-9127
8. Meredith, P.; Riesz, J. Radiative Relaxation Quantum Yields for Synthetic Eumelanin Photochem. Photobiol. 2004, 79, 211-216
9. Olsen, S.; Riesz, J.; Mahadevan, I.; Coutts, A.; Bothma, J. P.; Powell, B. J.; McKenzie, R. H.; Smith, S. C.; Meredith, P. Convergent Proton-Transfer Photocycles Violate Mirror-Image Symmetry in a Key Melanin Monomer J. Am. Chem. Soc. 2007, 129, 6672-6673
10. Edge, R.; d'Ischia, M.; Land, E. J.; Napolitano, A.; Navaratnam, S.; Panzella, L.; Pezzella, A.; Ramsden, C. A.; Riley, P. A. Dopaquinone Redox Exchange with Dihydroxyindole and Dihydroxyindole Carboxylic Acid Pigm. Cell Res. 2006, 19, 443-450
11. Gauden, M.; Pezzella, A.; Panzella, L.; Neves-Petersen, M. T.; Skovsen, E.; Petersen, S. B.; Mullen, K. M.; Napolitano, A.; d'Ischia, M.; Sundstrom, V. Role of Solvent, pH, and Molecular Size in Excited-State Deactivation of Key Eumelanin Building Blocks: Implications for Melanin Pigment Photostability J. Am. Chem. Soc. 2008, 130, 17038-17043
12. Bangal, P. R.; Chakravorti, S. Excited State Proton Transfer in Indole-2-Carboxylic Acid and Indole-5-Carboxylic Acid J. Phys. Chem. A 1999, 103, 8585-8594
13. Huijser, A.; Rode, M. F.; Corani, A.; Sobolewski, A. L.; Sundstrom, V. Photophysics of Indole-2-Carboxylic Acid in an Aqueous Environment Studied by Fluorescence Spectroscopy in Combination with Ab Initio Calculations Phys. Chem. Chem. Phys. 2012, 14, 2078-2086
14. Jimenez, R.; Fleming, G. R.; Kumar, P. V.; Maroncelli, M. Femtosecond Solvation Dynamics of Water Nature 1994, 369, 471-473
15. Rosenthal, S. J.; Jimenez, R.; Fleming, G. R.; Kumar, P. V.; Maroncelli, M. Solvation Dynamics in Methanol-Experimental and Molecular-Dynamics Simulation Studies J. Mol. Liq. 1994, 60, 25-56
16. Presiado, I.; Erez, Y.; Huppert, D. Excited-State Intermolecular Proton Transfer of the Firefly's Chromophore d -Luciferin. 2. Water-Methanol Mixtures J. Phys. Chem. A 2010, 114, 9471-9479
17. Manz, T.; Wörste, L. Femtosecond Intramolecular Proton Transfer in Condensed Phase. Femtosecond Chemistry; VCH: Weinheim, Germany, 1995; p 563.
18. Lochbrunner, S.; Wurzer, A. J.; Riedle, E. Microscopic Mechanism of Ultrafast Excited-State Intramolecular Proton Transfer: A 30-fs Study of 2-(2′-Hydroxyphenyl)Benzothiazole J. Phys. Chem. A 2003, 107, 10580-10590
19. Bhattacharya, B.; Samanta, A. Excited-State Proton-Transfer Dynamics of 7-Hydroxyquinoline in Room Temperature Ionic Liquids J. Phys. Chem. B 2008, 112, 10101-10106
20. Kang, B. T.; Ko, K. C.; Park, S. Y.; Jang, D. J.; Lee, J. Y. Solvent Effect on the Excited-State Proton Transfer of 7-Hydroxyquinoline Along a Hydrogen-Bonded Ethanol Dimer Phys. Chem. Chem. Phys. 2011, 13, 6332-6339
21. Konijnenberg, J.; Ekelmans, G. B.; Huizer, A. H.; Varma, C. A. G. O. Mechanism and Solvent Dependence of the Solvent-Catalyzed Pseudo-Intramolecular Proton-Transfer of 7-Hydroxyquinoline in the 1st Electronically Excited Singlet-State and in the Ground-State of Its Tautomer J. Chem. Soc., Faraday Trans. 2 1989, 85, 39-51
22. Manca, C.; Tanner, C.; Leutwyler, S. Excited State Hydrogen Atom Transfer in Ammonia-Wire and Water-Wire Clusters Int. Rev. Phys. Chem. 2005, 24, 457-488
23. Brejc, K.; Sixma, T. K.; Kitts, P. A.; Kain, S. R.; Tsien, R. Y.; Ormo, M.; Remington, S. J. Structural Basis for Dual Excitation and Photoisomerization of the Aequorea Victoria Green Fluorescent Protein Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2306-2311
24. Luecke, H.; Schobert, B.; Richter, H. T.; Cartailler, J. P.; Lanyi, J. K. Structural Changes in Bacteriorhodopsin During Ion Transport at 2 Angstrom Resolution Science 1999, 286, 255-260
25. Stoner-Ma, D.; Jaye, A. A.; Matousek, P.; Towrie, M.; Meech, S. R.; Tonge, P. J. Observation of Excited-State Proton Transfer in Green Fluorescent Protein Using Ultrafast Vibrational Spectroscopy J. Am. Chem. Soc. 2005, 127, 2864-2865
26. Stowell, M. H. B.; McPhillips, T. M.; Rees, D. C.; Soltis, S. M.; Abresch, E.; Feher, G. Light-Induced Structural Changes in Photosynthetic Reaction Center: Implications for Mechanism of Electron-Proton Transfer Science 1997, 276, 812-816
27. Tolbert, L. M.; Harvey, L. C.; Lum, R. C. Excited-State Proton-Transfer from Hydroxyalkylnaphthols J. Phys. Chem. 1993, 97, 13335-13340
28. Tolbert, L. M.; Solntsev, K. M. Excited-State Proton Transfer: From Constrained Systems to Super Photoacids to Superfast Proton Transfer Acc. Chem. Res. 2002, 35, 19-27
29. Laws, W. R.; Brand, L. Analysis of 2-State Excited-State Reactions-Fluorescence Decay of 2-Naphthol J. Phys. Chem. 1979, 83, 795-802
30. Webb, S. P.; Philips, L. A.; Yeh, S. W.; Tolbert, L. M.; Clark, J. H. Picosecond Kinetics of the Excited-State, Proton-Transfer Reaction of 1-Naphthol in Water J. Phys. Chem. 1986, 90, 5154-5164
31. Domcke, W.; Sobolewski, A. L. Chemistry-Unraveling the Molecular Mechanisms of Photoacidity Science 2003, 302, 1693-1694
32. Tolbert, L. M.; Haubrich, J. E. Photoexcited Proton-Transfer from Enhanced Photoacids J. Am. Chem. Soc. 1994, 116, 10593-10600
33. Webb, S. P.; Yeh, S. W.; Philips, L. A.; Tolbert, L. M.; Tolbert, M. A.; Clark, J. H. Excited-State Proton-Transfer Dynamics in Hydroxybiphenyls and Naphthols Abstr. Pap. Am. Chem. Sco. 1984, 188, 116
34. Kosower, E. M.; Huppert, D. Excited-State Electron and Proton Transfers Annu. Rev. Phys. Chem. 1986, 37, 127-156
35. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3rd ed.; Springer: New York, 2006.
36. Charkoudian, L. K.; Franz, K. J. Fe(III)-Coordination Properties of Neuromelanin Components: 5,6-Dihydroxyindole and 5,6-Dihydroxyindole-2- Carboxylic Acid Inorg. Chem. 2006, 45, 3657-3664
37. Cohen, B.; Segal, J.; Huppert, D. Proton Transfer from Photoacid to Solvent J. Phys. Chem. A 2002, 106, 7462-7467