Excited state intramolecular proton transfer reaction of 4′- N, N -diethylamino-3-hydroxyflavone and solvation dynamics in room temperature ionic liquids studied by optical kerr gate fluorescence measurement

Journal of Physical Chemistry B

Volumn 114, Issue 36, 2010, Pages 11847-11858

  Kimura, Yoshifumi ^a   Fukuda, Masanori ^a   Suda, Kayo ^a   Terazima, Masahide ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; AMIDES; DECAY (ORGANIC); DYNAMICS; FLUORESCENCE; IONIC LIQUIDS; IONS; ORGANIC SOLVENTS; PHOTOEXCITATION; PROTON TRANSFER; SOLVATION;

3-HYDROXYFLAVONE; ACTIVATION PROCESS; ANION SPECIES; BIEXPONENTIAL FUNCTIONS; DECAY COMPONENTS; DELAY TIME; DUAL FLUORESCENCE; ELECTRONIC EXCITED STATE; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; FLUORESCENCE COMPONENTS; FLUORESCENCE DYNAMICS; FLUORESCENCE MEASUREMENTS; FLUORESCENCE PEAK; FLUORESCENCE SPECTRA; FRANCK-CONDON; METHOXY; NONRADIATIVE PROCESS; NORMAL COMPONENT; NORMAL FORM; NORMAL STATE; OPTICAL KERR GATE; POPULATION CHANGE; PROBE MOLECULES; RELATIVE INTENSITY; ROOM TEMPERATURE IONIC LIQUIDS; SINGLE BAND; SOLVATION DYNAMICS; SOLVATION TIME; TIME CONSTANTS;

EXCITED STATES;

EID: 77956526187     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp105033q     Document Type: Article

References (74)

1. Nitzan, A. Chemical Dynamics in Condensed Phases Relaxation, Transfer, and Reactions in Condensed Molecular Systems; Oxford University Press: Oxford, U.K., 2006.
2. Karmakar, R.; Samanta, A. J. Phys. Chem. A 2002, 106, 4447
3. Ito, N.; Arzhantsev, S.; Heitz, M.; Maroncelli, M. J. Phys. Chem. B 2004, 108, 5771
4. Ingram, J. A.; Moog, R. S.; Ito, N.; Biswas, R.; Maroncelli, M. J. Phys. Chem. B 2003, 107, 5926
5. Arzhantsev, S.; Ito, N.; Heitz, M.; Maroncelli, M. Chem. Phys. Lett. 2003, 381, 278
6. Karmakar, R.; Samanta, A. J. Phys. Chem. A 2003, 107, 7340
7. Seth, D.; Chakraborty, A.; Setua, P.; Sarkar, N. J. Phys. Chem. B 2007, 111, 4781
8. Arzhantsev, S.; Jin, H.; Baker, G. A.; Maroncelli, M. J. Phys. Chem. B 2007, 111, 4978
9. Jin, H.; Baker, G. A.; Arzahantsev, S.; Dong, J.; Maroncelli, M. J. Phys. Chem. B 2007, 111, 7291
10. Paul, A.; Samanta, A. J. Phys. Chem. B 2007, 111, 4724
11. Shim, Y.; Duan, J. S.; Choi, M. Y.; Kim, H. J. J. Chem. Phys. 2003, 119, 6411
12. Shim, Y.; Choi, M. Y.; Kim, H. J. J. Chem. Phys. 2005, 122 044511
13. Kobrak, M. N. J. Chem. Phys. 2006, 125 064502
14. Iwata, K.; Okajima, H.; Saha, S.; Hamaguchi, H. Acc. Chem. Res. 2007, 40, 1174
15. Shigeto, S.; Hamaguchi, H. Chem. Phys. Lett. 2006, 427, 329
16. Wang, Y.; Voth, G. A. J. Am. Chem. Soc. 2005, 127, 12192
17. Wang, Y.; Voth, G. A. J. Phys. Chem. B 2006, 110, 18601
18. Lopes, J. N. A. C.; Pádua, A. A. H. J. Phys. Chem. B 2006, 110, 3330
19. Hu, Z.; Margulis, C. J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 831
20. Nagasawa, Y.; Itoh, T.; Yasuda, M.; Ishibashi, Y.; Ito, S.; Miyasaka, H. J. Phys. Chem. B 2008, 112, 15758
21. Bhattacharya, B.; Samanta, A. J. Phys. Chem. B 2008, 112, 10101
22. Chou, P. T.; Pu, S. C.; Cheng, Y. M.; Yu, W. S.; Yu, Y. C.; Hung, F. T.; Hu, W. P. J. Phys. Chem. A 2005, 109, 3777
23. Cheng, Y. M.; Pu, S. C.; Yu, Y. C.; Chou, P. T.; Huang, C. H.; Chen, C. T.; Li, T. H.; Hu, W. P. J. Phys. Chem. A 2005, 109, 11696
24. Chou, P. T.; Huang, C. H.; Hu, S. C.; Cheng, Y. M.; Liu, Y. H.; Wang, Y.; Chen, C. T. J. Phys. Chem. A 2004, 108, 6452
25. Klymchenko, A. S.; Demchenko, A. P. Phys. Chem. Chem. Phys. 2003, 5, 461
26. Klymchenko, A. S.; Oxturk, T.; Demchenko, A. P. Tetrahedron Lett. 2002, 43, 7079
27. Klymchenko, A. S.; Demchenko, A. P. J. Am. Chem. Soc. 2002, 124, 12372
28. Shynkar, V. V.; Mely, Y.; Duportail, G.; Piemont, E.; Klymchenko, A. S.; Demchenko, A. P. J. Phys. Chem. A 2003, 107, 9522
29. Yushchenko, D. A.; Shvadchak, V. V.; Klymchenko, A. S.; Duportail, G.; Pivovarenko, V. G.; Mely, Y. J. Phys. Chem. A 2007, 111, 10435
30. Ormson, S. M.; Brown, R. G.; Vollmer, F.; Rettig, W. J. Photochem. Photobiol., A 1994, 81, 65
31. Ameer, B. S.; Ormson, S. M.; Poteau, X.; Brown, R. G.; Foggi, P.; Bussotti, L.; Neuwahl, F. V. R. J. Phys. Chem. A 2004, 108, 6938
32. Ormson, S. M.; Legourrierec, D.; Brown, R. G.; Foggi, P. J. Chem. Soc., Chem. Commun. 1995, 20, 2133
33. Swinney, T. C.; Kelley, D. F. J. Chem. Phys. 1993, 99, 211
34. Parsapour, F.; Kelly, D. F. J. Phys. Chem. 1996, 100, 2791
35. Brucker, G. A.; Kelley, D. F. J. Phys. Chem. 1988, 92, 3805
36. Brucker, G. A.; Swinney, T. C.; Kelley, D. F. J. Phys. Chem. 1991, 95, 3190
37. Swinney, T. C.; Kelley, D. F. J. Phys. Chem. 1991, 95, 10369
38. Douhal, A.; Sanz, M.; Tormo, L.; Organero, J. A. ChemPhysChem 2005, 6, 419
39. Douhal, A.; Sanz, M.; Carranza, M. A.; Organero, J. A.; Santos, L. Chem. Phys. Lett. 2004, 394, 54
40. Roshal, A. D.; Organero, J. A.; Douhal, A. Chem. Phys. Lett. 2003, 379, 53
41. Sanz, M.; Organero, J. A.; Douhal, A. Chem. Phys. 2007, 338, 135
42. Ameer, B. S.; Ormson, S. M.; Brown, R. G.; Matousek, P.; Towrie, M.; Nibbering, E. T. J.; Foggi, P.; Neuwahl, F. V. R. J. Phys. Chem. A 2001, 105, 3709
43. Fukuda, M.; Terazima, M.; Kimura, Y. Chem. Phys. Lett. 2008, 463, 364
44. Smith, M. A.; Neumann, R. M.; Webb, R. A. J. Heterocyclic Chem. 1968, 5, 425
45. Arzhabtsev, S.; Maroncelli, M. Appl. Spectrosc. 2005, 59, 206
46. The sensitivity calibration using another set of dyes (tetraphenylbutadiene, coumarin 153, and DCM) was also performed for the Kerr gate system, as is described in ref 45. No significant difference has been detected for the wavelength region used in our study.
47. In the previous paper (ref 43), we used the different definition of the log-normal function, I (?) = h exp [ - { ln (? / ? p) / δ } 2 ] which does not have the asymmetric parameter ?. In the present paper, we used the conventional definition of the log-normal function as eq 1.
48. Fujisawa, T.; Fukuda, M.; Terazima, M.; Kimura, Y. J. Phys. Chem. A 2006, 110, 6164
49. Kimura, Y.; Hamamoto, T.; Terazima, M. J. Phys. Chem. A 2007, 111, 7081
50. Tokuda, H.; Hayamizu, K.; Ishii, K.; Susan, M. A. B. H.; Watanabe, M. J. Phys. Chem. B 2004, 108, 16593
51. Tokuda, H.; Ishii, K.; Susan, M. A. B. H.; Tsuzuki, S.; Hayamizu, K.; Watanabe, M. J. Phys. Chem. B 2006, 110, 2833
52. Noda, A.; Hayamizu, K.; Watanabe, M. J. Phys. Chem. B 2001, 105, 4603
53. Tariq, M.; Forte, P. A. S.; Gomes, C.; Lopes, J. N. C.; Rebelo, L. P. N. J. Chem. Thermodyn. 2009, 41, 790
54. Kagaku-Binran, 5 th ed.; Chemical Society of Japan: Maruzen, Tokyo, 2004.
55. Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. J. Phys. Chem. 1995, 99, 17311
56. 2].
57. fast. We used this procedure because the time resolution and the signal-to-noise ratio in the previous report were not enough to make the global analysis. However, the assumption used in the previous paper was not good to evaluate the population dynamics, and in the present paper, we have changed the way of the analysis to make the global fitting using the data of normal decay and tautomer rise simultaneously.
58. Daguenet, C.; Dynon, P. J.; Krossing, I.; Oleinikova, A.; Slattery, J.; Wakai, C.; Weingärtner, H. J. Phys. Chem. B 2006, 110, 12682
59. Weingärtner, H.; Sasisanker, P.; Daguenet, C.; Dyson, P. J.; Krossing, I.; Slattery, J. M.; Schubert, T. J. Phys. Chem. B 2007, 111, 4775
60. Itoh, M.; Fujiwara, Y.; Sumitani, M.; Yoshihara, K. J. Phys. Chem. 1986, 90, 5672
61. Ozawa, R.; Hamaguchi, H. Chem. Lett. 2001, 736
62. Fukuda, M.; Kajimoto, O.; Terazima, M.; Kimura, Y. J. Mol. Liq. 2007, 134, 49
63. Ionic Liquids in Synthesis, 2 nd ed.; Wasserschid, P.; Welton, T., Eds.; Wiley-VCH Verlag GmBH & Co. KGaA: Weinheim, Germany, 2008.
64. Cammarata, L.; Kazarian, S. G.; Salter, P. A.; Welton, T. Phys. Chem. Chem. Phys. 2001, 3, 5192
65. Kimura, Y.; Kobayashi, A.; Osawa, K.; Terazima, M. Manuscript in preparation.
66. Sumi, H.; Marcus, R. A. J. Chem. Phys. 1986, 84, 4894
67. Shim, Y.; Kim, H. J. J. Phys. Chem. B 2009, 113, 4510
68. Pison, L.; Lopes, J. N. C.; Rebelo, L. P.; Pádua, A. A. H.; Costa Gomes, M. F. J. Phys. Chem. B 2008, 112, 12394
69. Triolo, A.; Russina, O.; Bleif, H.-J.; Di Cola, E. J. Phys. Chem. B 2007, 111, 4641
70. Triolo, A.; Russina, O.; Fazio, B.; Appetecchi, G. B.; Carewska, M.; Passerini, S. J. Chem. Phys. 2009, 130, 164521
71. Mandal, P. K.; Sarkar, M.; Samanta, A. J. Phys. Chem. A 2004, 108, 9048
72. Paul, A.; Mandal, P. K.; Samanta, A. J. Phys. Chem. B 2005, 109, 9148
73. Jin, H.; Xiang, Li.; Maroncelli, M. J. Phys. Chem. B 2007, 111, 13473
74. Kimura, Y.; Hamamoto, T.; Terazima, M. J. Phys. Chem. A 2007, 111, 7081