Photochemical mechanisms of radiationless deactivation processes in urocanic acid

Journal of Physical Chemistry B

Volumn 118, Issue 4, 2014, Pages 976-985

  Tuna, Deniz ^a   Sobolewski, Andrzej L ^b   Domcke, Wolfgang ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b INSTITUTE OF PHYSICS   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; ISOMERS; PHOTOCHEMICAL REACTIONS;

AB INITIO INVESTIGATION; COMPUTATIONAL STUDIES; EXCITATION WAVELENGTH; EXCITED STATE REACTIONS; EXCITED-STATE DYNAMICS; PHOTOCHEMICAL MECHANISM; PHOTOCHEMICAL PROCESS; RADIATIONLESS DEACTIVATION;

EXCITED STATES;

UROCANIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY; QUANTUM THEORY; STEREOISOMERISM;

MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; QUANTUM THEORY; STEREOISOMERISM; UROCANIC ACID;

EID: 84893513459     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp411818j     Document Type: Article

References (56)

1. Mohammad, T.; Morrison, H.; HogenEsch, H. Urocanic Acid Photochemistry and Photobiology Photochem. Photobiol. 1999, 69, 115-135
2. Simon, J. D. Spectroscopic and Dynamic Studies of the Epidermal Chromophores trans -Urocanic Acid and Eumelanin Acc. Chem. Res. 2000, 33, 307-313
3. Gibbs, N. K.; Tye, J.; Norval, M. Recent Advances in Urocanic Acid Photochemistry, Photobiology and Photoimmunology Photochem. Photobiol. Sci. 2008, 7, 655-667
4. Gibbs, N. K.; Norval, M. Urocanic Acid in the Skin: A Mixed Blessing? J. Invest. Dermatol. 2011, 131, 14-17
5. Morrison, H.; Bernasconi, C.; Pandey, G. A Wavelength Effect on Urocanic Acid E / Z Photoisomerization Photochem. Photobiol. 1984, 40, 549-550
6. Laihia, J. K.; Lemmetyinen, H.; Pasanen, P.; Jansén, C. T. Establishment of a Kinetic Model for Urocanic Acid Photoisomerization J. Photochem. Photobiol., B 1996, 33, 211-217
7. Li, B.; Hanson, K. M.; Simon, J. D. Primary Processes of the Electronic Excited States of trans -Urocanic Acid J. Phys. Chem. A 1997, 101, 969-972
8. Hanson, K. M.; Li, B.; Simon, J. D. A Spectroscopic Study of the Epidermal Ultraviolet Chromophore trans -Urocanic Acid J. Am. Chem. Soc. 1997, 119, 2715-2721
9. Hanson, K. M.; Simon, J. D. The Origin of the Wavelength-Dependent Photoreactivity of trans -Urocanic Acid Photochem. Photobiol. 1998, 67, 538-540
10. Kammeyer, A.; Eggelte, T. A.; Bos, J. D.; Teunissen, M. B. M. Urocanic Acid Isomers are Good Hydroxyl Radical Scavengers: A Comparative Study with Structural Analogues and with Uric Acid Biochim. Biophys. Acta 1999, 1428, 117-120
11. Haralampus-Grynaviski, N.; Ransom, C.; Ye, T.; Roîzanowska, M.; Wrona, M.; Sarna, T.; Simon, J. D. Photogeneration and Quenching of Reactive Oxygen Species by Urocanic Acid J. Am. Chem. Soc. 2002, 124, 3461-3468
12. Brookman, J.; Chaćon, J. N.; Sinclair, R. S. Some Photophysical Studies of cis-and trans -Urocanic Acid Photochem. Photobiol. Sci. 2002, 1, 327-332
13. Menon, E. L.; Morrison, H. Formation of Singlet Oxygen by Urocanic Acid by UVA Irradiation and Some Consequences Thereof Photochem. Photobiol. 2002, 75, 565-569
14. Schwarzinger, B.; Falk, H. Concerning the Photodiastereomerization and Protic Equilibria of Urocanic Acid and its Complex with Human Serum Albumin Monatsh. Chem. 2004, 135, 1297-1304
15. Wallis, R. A.; Smith, G. J.; Dunford, C. L. The Effect of Molecular Environment on the Photoisomerization of Urocanic Acid Photochem. Photobiol. 2004, 80, 257-261
16. Baier, J.; Maisch, T.; Engel, E.; Landthaler, M.; Bäumler, W. Singlet Oxygen Generation by UVA Light Exposure of Endogenous Photosensitizers Biophys. J. 2006, 91, 1452-1459
17. Egawa, M.; Nomura, J.; Iwaki, H. The Evaluation of the Amount of cis-and trans -Urocanic Acid in the Stratum Corneum by Raman Spectroscopy Photochem. Photobiol. Sci. 2010, 9, 730-733
18. Ryan, W. L.; Levy, D. H. Electronic Spectroscopy and Photoisomerization of trans -Urocanic Acid in a Supersonic Jet J. Am. Chem. Soc. 2001, 123, 961-966
19. Shukla, M. K.; Mishra, P. C. Electronic Spectra, Structure and Photoisomerization of Urocanic Acid Spectrochim. Acta 1995, 51A, 831-838
20. Lahti, A.; Hotokka, M.; Neuvonen, K.; Äyräs, P. A Theoretical Study of the Conformers of trans-and cis -Urocanic Acid J. Mol. Struct.: THEOCHEM 1995, 331, 169-179
21. Lahti, A.; Hotokka, M.; Neuvonen, K.; Äyräs, P. Quantum-Chemical Gas-Phase Calculations on the Protonation Forms of trans-and cis -Urocanic Acid Struct. Chem. 1997, 8, 331-342
22. Lahti, A.; Hotokka, M.; Neuvonen, K.; Karlström, G. Quantum Chemical Calculations on the Intramolecular Hydrogen Bond of cis -Urocanic Acid J. Mol. Struct.: THEOCHEM 1998, 452, 185-202
23. Lahti, A.; Hotokka, M.; Neuvonen, K.; Karlström, G. A CASSCF Study on the Lowest π → π * Excitation of Urocanic Acid Int. J. Quantum Chem. 1999, 72, 25-37
24. Page, C. S.; Merchán, M.; Serrano-Andrés, L.; Olivucci, M. A Theoretical Study of the Low-Lying Excited States of trans-and cis -Urocanic Acid J. Phys. Chem. A 1999, 103, 9864-9871
25. Page, C. S.; Olivucci, M.; Merchán, M. A Theoretical Study of the Low-Lying States of the Anionic and Protonated Ionic Forms of Urocanic Acid J. Phys. Chem. A 2000, 104, 8796-8805
26. Danielsson, J.; Uličný, J.; Laaksonen, A. A TD-DFT Study of the Photochemistry of Urocanic Acid in Biologically Relevant Ionic, Rotameric, and Protomeric Forms J. Am. Chem. Soc. 2001, 123, 9817-9821
27. Danielsson, J.; Söderhall, J. A.; Laaksonen, A. Hydration Structure and Conformational Dynamics of Urocanic Acid: A Computer Simulation Study Mol. Phys. 2002, 100, 1873-1886
28. Danielsson, J.; Laaksonen, A. Gas Phase Photoisomerization of Urocanic Acid-A Theoretical Study Chem. Phys. Lett. 2003, 370, 625-630
29. Dmitrenko, O.; Reischl, W.; Bach, R. D.; Spanget-Larsen, J. TD-DFT Computational Insight into the Origin of Wavelength-Dependent E / Z Photoisomerization of Urocanic Acid J. Phys. Chem. A 2004, 108, 5662-5669
30. Shen, L.; Ji, H.-F. Theoretical Investigation of the Photosensitization Mechanisms of Urocanic Acid J. Photochem. Photobiol., B 2008, 91, 96-98
31. Tiwari, S.; Mishra, P. C. Urocanic Acid as an Efficient Hydroxyl Radical Scavenger: A Quantum Theoretical Study J. Mol. Model. 2011, 17, 59-72
32. Barbatti, M. The Role of Tautomers in the UV Absorption of Urocanic Acid Phys. Chem. Chem. Phys. 2011, 13, 4686-4692
33. Klessinger, M.; Michl, J. Excited States and Photochemistry of Organic Molecules; VCH Publishers: New York, 1995.
34. Conical Intersections: Electronic Structure, Dynamics & Spectroscopy; Domcke, W.; Yarkony, D. R.; Köppel, H., Eds.; World Scientific Publishing: Singapore, 2004.
35. Computational Photochemistry; Olivucci, M., Ed.; Elsevier: Amsterdam, 2005.
36. Conical Intersections: Theory, Computation and Experiment; Domcke, W.; Yarkony, D. R.; Köppel, H., Eds.; World Scientific Publishing: Singapore, 2011.
37. Atchity, G. J.; Xantheas, S. S.; Ruedenberg, K. Potential Energy Surfaces Near Intersections J. Chem. Phys. 1991, 95, 1862-1876
38. Quenneville, J.; Martínez, T. J. Ab Initio Study of cis-trans Photoisomerization in Stilbene and Ethylene J. Phys. Chem. A 2003, 107, 829-837
39. Barbatti, M.; Lischka, H.; Salzmann, S.; Marian, C. M. UV Excitation and Radiationless Deactivation of Imidazole J. Chem. Phys. 2009, 130, 034305
40. Crespo-Otero, R.; Barbatti, M.; Yu, H.; Evans, N. L.; Ullrich, S. Ultrafast Dynamics of UV-Excited Imidazole ChemPhysChem 2011, 12, 3365-3375
41. Hadden, D. J.; Wells, K. L.; Roberts, G. M.; Bergendahl, L. T.; Paterson, M. J.; Stavros, V. G. Time Resolved Velocity Map Imaging of H-Atom Elimination from Photoexcited Imidazole and its Methyl Substituted Derivatives Phys. Chem. Chem. Phys. 2011, 13, 10342-10349
42. Yu, H.; Evans, N. L.; Stavros, V. G.; Ullrich, S. Investigation of Multiple Electronic Excited State Relaxation Pathways Following 200 nm Photolysis of Gas-Phase Imidazole Phys. Chem. Chem. Phys. 2012, 14, 6266-6272
43. Serrano-Andrés, L.; Merchán, M. Quantum Chemistry of the Excited State: 2005 Overview J. Mol. Struct.: THEOCHEM 2005, 729, 99-108
44. Martínez, T. J. Insights for Light-Driven Molecular Devices from Ab Initio Multiple Spawning Excited-State Dynamics of Organic and Biological Chromophores Acc. Chem. Res. 2006, 39, 119-126
45. Barbatti, M.; Aquino, A. J. A.; Szymczak, J. J.; Nachtigallová, D.; Hobza, P.; Lischka, H. Relaxation Mechanisms of UV-Photoexcited DNA and RNA Nucleobases Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 21453-21458
46. Schapiro, I.; Ryazantsev, M. N.; Frutos, L. M.; Ferré, N.; Lindh, R.; Olivucci, M. The Ultrafast Photoisomerizations of Rhodopsin and Bathorhodopsin Are Modulated by Bond Length Alternation and HOOP Driven Electronic Effects J. Am. Chem. Soc. 2011, 133, 3354-3364
47. Lasorne, B.; Worth, G. A.; Robb, M. A. Excited-State Dynamics WIREs Comput. Mol. Sci. 2011, 1, 460-475
48. Lan, Z.; Lou, Y.; Fabiano, E.; Thiel, W. QM/MM Nonadiabatic Decay Dynamics of 9H-Adenine in Aqueous Solution ChemPhysChem 2011, 12, 1989-1998
49. Mališ, M.; Loquais, Y.; Gloaguen, E.; Biswal, H. S.; Piuzzi, F.; Tardivel, B.; Brenner, V.; Broquier, M.; Jouvet, C.; Mons, M. Unraveling the Mechanisms of Nonradiative Deactivation in Model Peptides Following Photoexcitation of a Phenylalanine Residue J. Am. Chem. Soc. 2012, 134, 20340-20351
50. Kuhlman, T. S.; Glover, W. J.; Mori, T.; Møller, K. B.; Martínez, T. J. Between Ethylene and Polyenes-The Nonadiabatic Dynamics of cis -Dienes Faraday Discuss. 2012, 157, 193-212
51. Plasser, F.; Barbatti, M.; Aquino, A. J. A.; Lischka, H. Electronically Excited States and Photodynamics: A Continuing Challenge Theor. Chem. Acc. 2012, 131, 1073-1087
52. Ashfold, M. N. R.; King, G. A.; Murdock, D.; Nix, M. G. D.; Oliver, T. A. A.; Sage, A. G. πσ * Excited States in Molecular Photochemistry Phys. Chem. Chem. Phys. 2010, 12, 1218-1238
53. Sellner, B.; Barbatti, M.; Müller, T.; Domcke, W.; Lischka, H. Ultrafast Non-Adiabatic Dynamics of Ethylene Including Rydberg States Mol. Phys. 2013, 111, 2439-2450
54. TURBOMOLE V6.3.1 2011, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007, available from http://www.turbomole.com.
55. Aquilante, F.; Vico, L. D.; Ferré, N.; Ghigo, G.; Malmqvist, P.-Å.; Neogrády, P.; Pedersen, T. B.; Pitonak, M.; Reiher, M.; Roos, B. O. MOLCAS 7: The Next Generation J. Comput. Chem. 2010, 31, 224-247
56. Lischka, H.; Shepard, R.; Shavitt, I.; Pitzer, R. M.; Dallos, M.; Müller, T.; Szalay, P. G.; Brown, F. B.; Ahlrichs, R.; Böhm, H. J.; COLUMBUS, an ab initio electronic structure program, release 7.0., 2012.