A genuine intramolecular proton relay system undergoing excited-state double proton transfer reaction

Journal of Physical Chemistry Letters

Volumn 2, Issue 24, 2011, Pages 3063-3068

  Tang, Kuo Chun ^a   Chen, Chyi Lin ^a   Chuang, Hsiao Han ^b   Chen, Jien Lian ^b   Chen, Yi Ju ^a   Lin, Yi Chih ^a   Shen, Jiun Yi ^a   Hu, Wei Ping ^b   Chou, Pi Tai ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

Clusters; Dynamics; Excited States

Indexed keywords

CLUSTERS; DOUBLE PROTON TRANSFER; ELECTRONIC EXCITED STATE; EXCITED-STATE INTRAMOLECULAR DOUBLE PROTON TRANSFERS; INTRAMOLECULAR HYDROGEN BOND; OVERALL RATE; PROTON-RELAY SYSTEMS; SYSTEM RESPONSE; THEORETICAL APPROACH;

CARBOXYLIC ACIDS; CHARGE TRANSFER; DYNAMICS; PROTONS;

EXCITED STATES;

EID: 84863323580     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz201439w     Document Type: Article

References (56)

1. Waluk, J. Hydrogen-Bonding-Induced Phenomena in Bifunctional Heteroazaaromatics. Acc. Chem. Res. 2003, 36, 832-838.
2. Tanner, C; Manca, C; Leutwyler, S. Probing the Threshold to H Atom Transfer along a Hydrogen-Bonded Ammonia Wire. Science 2003, 302, 1736-1739.
3. 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.
4. Paterson, M. J.; Robb, M. A; Blancafort, L.; DeBellis, A. D. Theoretical Study of Benzotriazole UV Photostability: Ultrafast Deactivation through Coupled Proton and Electron Transfer Triggered by a Charge-Transfer State. J. Am. Chem. Soc. 2004, 126, 2912-2922.
5. Hosoi, H.; Mizuno, H.; Miyawaki, A; Tahara, T. Competition between Energy and Proton Transfer in Ultrafast Excited-State Dynamics of an Oligomeric Fluorescent Protein Red Kaede. J. Phys. Chem.B 2006, 110, 22853-22860.
6. Wu, P.-W.; Hsieh, W.-T.; Cheng, Y.-M.; Wei, C-Y.; Chou, P.-T. Synthesis of 7-Azaserotonin: Its Photophysical Properties Associated with Excited State Proton Transfer Reaction. J. Am. Chem. Soc. 2006, 128, 14426-14427.
7. Kwon, O.-H.; Jang, D.-J. Excited-State Double Proton Transfer of 7-Azaindole in Water Nanopools. J. Phys. Chem. A 2005, 109, 20479-20484.
8. Gelabert, R; Moreno, M.; Lluch, J. M. Charge-Transfer ππ* Excited State in the 7-Azaindole Dimer. A Hybrid Configuration Interactions Singles/Time-Dependent Density Functional Theory Description. J. Phys. Chem. A 2006, 110, 1145-1151.
9. Barbatti, M.; Aquino, A. J. A; Lischka, H.; Schriever, C; Lochbrunner, S.; Riedle, E. Ultrafast Internal Conversion Pathway and Mechanism in 2-(2′-Hydroxyphenyl)benzothiazole: A Case Study for Excited-State Intramolecular Proton Transfer Systems. Phys. Chem. Chem. Phys. 2009, 11, 1406-1415.
10. Hsieh, C.-C.; Jiang, C.-M.; Chou, P.-T. Recent Experimental Advances on Excited-State Intramolecular Proton Coupled Electron Transfer Reaction. Acc. Chem. Res. 2010, 43, 1364-1374.
11. Demchenko, A. P. Protein Fluorescence, Dynamics and Function: Exploration of Analogy between Electronically Excited and Biocatalytic Transition States. Biochim. Biophys.Acta 1994, 1209, 149-164.
12. Demchenko, A. P. Visualization and Sensing of Intermolecular Interactions with Two-Color Fluorescent Probes. FEBS Lett. 2006, 580, 2951-2957.
13. Demchenko, A. P; Klymchenko, A. S.; Pivovarenko, V. G.; Ercelen, S.; Duportail, G; Mely, Y. Multiparametric Color-Changing Fluorescence Probes. J. Fluoresc. 2003, 13, 291-295.
14. Chou, H-C; Hsu, C.-H.; Cheng Y.-M.; Cheng C.-C; Liu, H.-W.; Pu, S.-C; Chou, P.-T. Multiple Hydrogen Bonds Tuning Guest/Host Excited-State Proton Transfer Reaction: Its Application in Molecular Recognition. J. Am. Chem. Soc. 2004, 126, 1650-1651.
15. Rodriguez-Rodriguez, C; de Groot, N. S.; Rimola, A; Alvarez-Larena, A; Lloveras, V.; Vidal-Gancedo, J.; Ventura, S.; Vendrell, J.; Sodupe, M.; Gonzalez-Duarte, P. Design, Selection, and Characterization of Thioflavin-Based Intercalation Compounds with Metal Chelating Properties for Application in Alzheimer's Disease. J. Am. Chem. Soc. 2009, 131, 1436-1451.
16. Tang, K.-C; Chang, M.-J.; Lin, T.-Y.; Pan, H.-A; Fang, T.-C.; Chen, K-Y.; Hung, W.-Y.; Hsu, Y-H; Chou, P.-T. Fine Tuning the Energetics of Excited-State Intramolecular Proton Transfer (ESIPT): White Light Generation in a Single ESIPT System. J. Am. Chem. Soc. 2011, 133, 17738-17745.
17. Chattoraj, M.; King, B. A; Bublitz, G U.; Boxer, S. G. Ultra-fast Excited State Dynamics in Green Fluorescent Protein: Multiple States and Proton Transfer. Proc. Natl Acad. Sci. U. S. A. 1996, 93, 8362-8367.
18. Cotlet, M.; Hofkens, J.; Kohn, F.; Michiels, J.; Dirix, G.; Van Guyse, M.; Vanderleyden, J.; De Schryver, F. C. Collective Effects in Individual Oligomers of the Red Fluorescent Coral Protein DsRed. Chem. Phys. Lett. 2001, 336, 415-423.
19. Hanson, G. T.; McAnaney, T. B.; Park, E. S.; Rendell, M.; Yarbrough, D. K.; Chu, S.; Xi, L.; Boxer, S. G.; Montrose, M. H.; Remington, S. J. Green Fluorescent Protein Variants as Ratiometric Dual Emission pH Sensors. 1. Structural Characterization and Preliminary Application. Biochemistry 2002, 41, 15477-15488.
20. Vendrell, O.; Gelabert, R.; Moreno, M.; Lluch, J. M. Photoinduced Proton Transfer from the Green Fluorescent Protein Chromophore to a Water Molecule: Analysis of the Transfer Coordinate. Chem. Phys. Lett. 2004, 396, 202-207.
21. Vendrell, O.; Gelabert, R.; Moreno, M.; Lluch, J. M. Potential Energy Landscape of the Photoinduced Multiple Proton-Transfer Process in the Green Fluorescent Protein: Classical Molecular Dynamics and Multiconfigurational Electronic Structure Calculations. J. Am. Chem. Soc. 2006, 128, 3564-3574.
22. Stoner-Ma, D.; Melief, E. H.; Nappa, J.; Ronayne, K. L.; Tonge, P. J.; Meech, S. R. Proton Relay Reaction in Green Fluorescent Protein (GFP): Polarization-Resolved Ultrafast Vibrational Spectroscopy of Isotopically Edited GFP. J. Phys. Chem. B 2006, 110, 22009-22018.
23. Stoner-Ma, D.; Jaye, A. A.; Ronayne, K. L.; Nappa, J.; Meech, S. R.; Tonge, P. J. An Alternate Proton Acceptor for Excited-State Proton Transfer in Green Fluorescent Protein: Rewiring GFP. J. Am. Chem. Soc. 2008, 130, 1227-1235.
24. Kondo, M.; Heisler, I. A.; Stoner-Ma, D.; Tonge, P. J.; Meech, S. R. Ultrafast Dynamics of Protein Proton Transfer on Short Hydrogen Bond Potential Energy Surfaces: S65T/H148D GFP. J. Am. Chem. Soc. 2010, 132, 1452-1453.
25. Hsieh, C.-C.; Chou, P.-T.; Shih, C.-W.; Chuang, W.-T.; Chung, M.-W.; Lee, J.; Joo, T. Comprehensive Studies on an Overall Proton Transfer Cycle of the ortho-Green Fluorescent Protein Chromophore. J. Am. Chem. Soc. 2011, 133, 2932-2943.
26. Taylor, C. A.; El-Bayoumi, M. A.; Kasha, M. Excited-State Two-Proton Tautomerism in Hydrogen-Bonded N-Heterocyclic Base Pairs. Proc. Natl. Acad. Sci. U. S. A. 1969, 103, 253-260.
27. Ingham, K. C.; El-Bayoumi, M. Photoinduced Double Proton Transfer in a Model Hydrogen Bonded Base Pair. Effects of Temperature and Deuterium Substitution. J. Am. Chem. Soc. 1974, 96, 1674-1682.
28. Takasugi, M.; Guendouz, A.; Chassignolt, M.; Decout, J. L.; Lhommet, J.; Thuong, N. T.; Helene, C. Sequence-Specific Photo-Induced Cross-Linking of the Two Strands of Double-Helical DNA by a Psoralen Covalently Linked to a Triple Helix-Forming Oligonucleotide. Proc. Natl. Acad. Sci. U. S. A 1991, 88, 5602-5606.
29. Crespo-Hernandez, C. E.; Cohen, B.; Hare, P. M.; Kohler, B. Ultrafast Excited-State Dynamics in Nucleic Acids. Chem. Rev. 2004, 104, 1977-2020.
30. Takeuchi, S.; Tahara, T. The Answer to Concerted versus Step-Wise Controversy for the Double Proton Transfer Mechanism of 7-Azaindole Dimer in Solution. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 5285-5290.
31. Kwon, O.-H.; Zewail, A. H. Double Proton Transfer Dynamics of Model DNA Base Pairs in the Condensed Phase. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 8703-8708.
32. 2h 7-Azaindole Dimer. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, E78.
33. Kwon, O.-H.; Zewail, A. H. Reply to Catalan: Double-Proton-Transfer Dynamics of Photo-Excited 7-Azaindole Dimers. Proc. Natl. Acad. Sci. U. S. A 2008, 105, E79 and references therein.
34. Itoh, M.; Adachi, T.; Tokumura, K. Time-Resolved Fluorescence and Absorption Spectra and Two-Step Laser excitation Fluorescence of the Excited-State Proton Transfer in the Methanol Solution of 7-Hydroxyquinoline. J. Am. Chem. Soc. 1984, 106, 850-855.
35. Lee, S.-I.; Jang, D.-J. Proton Transfers of Aqueous 7-Hydroxyquinoline in the First Excited Singlet, Lowest Triplet, and Ground States. J. Phys. Chem. 1995, 99, 7537-7541.
36. Lahmani, F.; Douhal, A.; Breheret, E.; Zehnacker-Rentien, A. Solvation Effects in Jet-Cooled 7-Hydroxyquinoline. Chem. Phys. Lett. 1994, 220, 235-242.
37. 2O)(n), n = 1-4. Chem. Phys. Lett. 1999, 299, 381-388.
38. Kohtani, S.; Tagami, A.; Nakagaki, R. Excited-State Proton Transfer of 7-Hydroxyquinoline in a Non-Polar Medium: Mechanism of Triple Proton Transfer in the Hydrogen-Bonded System. Chem. Phys. Lett. 2000, 316, 88-93.
39. Presiado, I.; Erez, Y.; Gepshtein, R.; Huppert, D. Excited-State Proton Transfer and Proton Reactions of 6-Hydroxyquinoline and 7-Hydroxyquinoline in Water and Ice. J. Phys. Chem. C 2009, 113, 20066-20075.
40. Bulska, H. Intramolecular Cooperative Double Proton Transfer in [2, 2′-Bipyridyl]-3, 3′-diol. Chem. Phys. Lett. 1983, 98, 398-402.
41. Mordzinski, A.; Grabowska, A.; Kuhnle, W.; Krowczynski, A. Intramolecular Single and Double Proton-Transfer in Benzoxazole Derivatives. Chem. Phys. Lett. 1983, 101, 291-296.
42. Zhang, H.; van der Meulen, P.; Glasbeek, M. Ultrafast Single and Double Proton Transfer in Photo-Excited [2, 2′-Bipyridyl]-3, 3′-diol. Chem. Phys. Lett. 1996, 253, 97-102.
43. Gelabert, R.; Moreno, M.; Lluch, J. M. Quantum Dynamics Study of the Excited-State Double-Proton Transfer in 2, 2′-Bipyridyl-3, 3′-diol. ChemPhysChem 2004, 5, 1372-1378.
44. Plasser, F.; Barbatti, M.; Aquino, A. J. A.; Lischka, H. Excited-State Diproton Transfer in [2, 2′-Bipyridyl]-3, 3′-diol: the Mechanism Is Sequential, Not Concerted. J. Phys. Chem. A 2009, 113, 8490-8499.
45. Douhal, A.; Kim, S. K.; Zewail, A. H. Femtosecond Molecular-Dynamics of Tautomerization in Model Base-Pairs. Nature 1995, 378, 260-263.
46. Folmer, D. E.; Poth, L.; Wisniewski, E. S.; Castleman, A. W. Arresting Intermediate States in A Chemical Reaction on a Femtosecond Time Scale: Proton Transfer in Model Base Pairs. Chem. Phys. Lett. 1998, 287, 1-7.
47. Chachisvilis, M.; Fiebig, T.; Douhal, A.; Zewail, A. H. Femtosecond Dynamics of a Hydrogen-Bonded Model Base Pair in the Condensed Phase: Double Proton Transfer in 7-Azaindole. J. Phys. Chem. A 1998, 102, 669-673.
48. Moreno, M.; Douhal, A.; Lluch, J. M. Ab Initio Based Exploration of the Potential Energy Surface for the Double Proton Transfer in the First Excited Singlet Electronic State of the 7-Azaindole Dimer. J. Phys. Chem. A 2001, 105, 3887-3893.
49. Guallar, V.; Batista, V. S.; Miller, W. H. Semiclassical Molecular Dynamics Simulations of Excited State Double-Proton Transfer in 7-Azaindole Dimers. J. Chem. Phys. 1999, 110, 9922-9936.
50. Takeuchi, S.; Tahara, T. Excitation-Wavelength Dependence of the Femtosecond Fluorescence Dynamics of 7-Azaindole Dimer: Further Evidence for the Concerted Double Proton Transfer in Solution. Chem. Phys. Lett. 2001, 347, 108-114.
51. Catalan, J.; Perez, P.; del Valle, J. C.; de Paz, J. L. G.; Kasha, M. H-Bonded N-Heterocyclic Base-Pair Phototautomerizational Potential Barrier and Mechanism: The 7-Azaindole Dimer. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 419-422.
52. Sakota, K.; Hara, A.; Sekiya, H. Excited-State Double-Proton Transfer Dynamics of Deuterated 7-Azaindole Dimers in a Free Jet Studied by Hole-Burning Spectroscopy. Phys. Chem. Chem. Phys. 2004, 6, 32-36.
53. Lim, H.; Park, S.-Y.; Jang, D.-J. Excited-State Double Proton Transfer Dynamics of Model DNA Base Pairs: 7-Hydroxyquinoline Dimers. J. Phys. Chem. A 2010, 114, 11432-11435.
54. Nagai, Y.; Saita, K.; Sakota, K.; Nanbu, S.; Sekine, M.; Nakata, M.; Sekiya, H. Electronic Spectra of Two Long-Lived Photoproducts: Double-Proton Transfer in 7-Hydroxyquinoline Dimer in a 2-Methyltetrahydrofuran Glass Matrix. J. Phys. Chem. A 2010, 114, 5041-5048.
55. Mishra, H.; Maheshwary, S.; Tripathi, H. B.; Sathyamurthy, N. An Experimental and Theoretical Investigation of the Photophysics of 1-Hydroxy-2-naphthoic Acid. J. Phys. Chem. A 2005, 109, 2746-2754.
56. Hu, W.-P.; Chen, J.-L.; Hsieh, C.-C.; Chou, P.-T. Theoretical Study on the Double Proton Transfer in a Hetero-Hydrogen-Bonded Dimer of 11-Propyl-6H-Indolo-[2, 3-b]Quinoline (6HIQ) and 7-Azaindole (7AI). Chem. Phys. Lett. 2010, 485, 226-230.