Solvent dependence of the spectra and kinetics of excited-state charge transfer in three (alkylamino)benzonitriles

Journal of Physical Chemistry B

Volumn 109, Issue 4, 2005, Pages 1563-1585

  Dahl, K ^b   Biswas, R ^c   Ito, N ^a   Maroncelli, M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

^c S N BOSE NATIONAL CENTRE FOR BASIC SCIENCES   (India)

Author keywords

[No Author keywords available]

Indexed keywords

(ALKYLAMINO)BENZONITRILES; EXCITED STATE; SOLUTES; SOLVATION;

ABSORPTION; CHARGE TRANSFER; ELECTRONIC STRUCTURE; FLUORESCENCE; FREE ENERGY; ORGANIC SOLVENTS; REACTION KINETICS; SURFACE REACTIONS;

NITROGEN COMPOUNDS;

EID: 13444287813     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp046605p     Document Type: Article

References (96)

1. Grabowski, Z. R.; Rotldewicz, K.; Rettig, W. Chem. Rev. 2003, 103, 3899.
2. Lippen, E; Rettig, W.; Bonacid-Koutecky, V.; Heisel, F.; Miehé, J. A. Adv. Chem. Phys. 1987, 68, 1.
3. Grabowski, Z. R.; Rotkiewicz, K.; Siemiarczuk, A.; Cowley, D. J.; Baumann, W. Nouv. J. Chim. 1979, 3, 443.
4. Zachariasse, K. A.; Druzhinin, S. L; Bosch, W.; Machinek, R. J. Am. Chem. Soc. 2004, 126, 1705.
5. Techert, S.; Zachariasse, K. A. J. Am. Chem. Soc. 2004, 126, 5593.
6. Zachariasse, K. A. Chem. Phys. Lett. 2000, 320, 8.
7. See also the recent proposal of an intermediate in: Zgierski, M. Z.; Lim, E. C. Chem. Phys. Lett. 2004, 393, 143.
8. Rettig, W. J. Luminesc. 1980, 26, 21.
9. Rettig, W. J. Phys. Chem. 1982, 86, 1970.
10. Rettig, W.; Gleiter, R. J. Phys. Chem. 1985, 89, 4674.
11. Rettig, W.; Wermuth, G. J. Photochem. 1985, 28, 351.
12. Al-Hassan, K. A.; Rettig, W. Chem. Phys. Lett. 1986, 126, 273.
13. LaFemina, J. P.; Duke, C. B.; Rettig, W. Chem. Phys. 1990, 87, 2151.
14. Rettig, W. Ber. Bunsen-Ges. Phys. Chem. 1991, 95, 259.
15. Baumann, W.; Bischof, H.; Frohling, J.-C.; Brittinger, C. J. Photochem. Photobiol. A 1992, 64, 49.
16. Braun, D.; Rettig, W. Chem. Phys. 1994, 180, 231.
17. Braun, D.; Rettig, W. Chem. Phys. Lett. 1997, 268, 110.
18. Yatsuhashi, T.; Troshin, S. A.; Fuss, W.; Rettig, W.; Schmid, W. E.; Zilberg, S. Chem. Phys. 2004, 296, 1.
19. Zachariasse, K. A.; Grobys, M.; von der Haar, T.; Hebecker, A.; Il'ichev, Y. V.; Jiang, Y.-B.; Morawski, O.; Kühnle, W. J. Photochem. Photobiol. A 1996, 102, 59.
20. von der Haar, T.; Hebecker, A.; Il'ichev, Y.; Jiang, Y.-B.; Kühnle, W.; Zachariasse, K. A. Rec. Trav. Chim. Pays-Bas 1995, 114, 430.
21. Zachariasse, K. A.; von der Haar, T.; Leinhos, U.; Kühnle, W. J. Inf. Rec. Mater. 1994, 21, 501.
22. Rettig, W.; Zietz, B. Chem. Phys. Lett. 2000, 317, 187.
23. W. Song and M. Maroncelli, unpublished results.
24. Parusel, A. B. J. Chem. Phys. Lett. 2001, 340, 531.
25. Heisel, F.; Miehé, J. A. Chem. Phys. Lett. 1983, 100, 183.
26. Heisel, F.; Miehé, J. A. Chem. Phys. 1985, 98, 233.
27. Heisel, F.; Miehé, J. A.; Martinho, J. M. G. Chem. Phys. 1985, 98, 243.
28. Su, S.-G.; Simon, J. D. J. Chem. Phys. 1988, 89, 908.
29. Stratt, R. M.; Maroncelli, M. J. Phys. Chem. 1996, 100, 12981.
30. Maroncelli, M. J. Mol. Liq. 1993, 57, 1.
31. Barbara, P. F.; Jarzeba, W. Adv. Photochem. 1990, 15, 1.
32. Hynes, J. T. Charge-Transfer Reactions and Solvation Dynamics. In Ultrafast Dynamics of Chemical Systems; Simon, J. D., Ed.; Kluwer: Dordrecht, 1994; p 345.
33. Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. J. Phys. Chem. 1995, 99, 17311.
34. Reynolds, L.; Gardecki, J. A.; Frankland, S. J. V.; Horng, M. L.; Maroncelli, M. J. Phys. Chem. 1996, 100, 10337.
35. Sumi, H.; Marcus, R. A. J. Chem. Phys. 1986, 84, 4894.
36. Nadler, W.; Marcus, R. A. J. Chem. Phys. 1987, 86, 3906.
37. Simon, J. D.; Doolen, R. J. Am. Chem. Soc. 1992, 114, 4861.
38. Moro, G. J.; Nordio, P. L.; Polimeno, A. Mol. Phys. 1989, 68, 1131.
39. Polimeno, A.; Barbon, A.; Nordio, P. L.; Rettig, W. J. Phys. Chem. 1994, 98, 12158.
40. Nordio, P. L.; Polimeno, A.; Saielli, G. J. Photochem. Photobiol. A 1997, 105, 269.
41. Nordio, P. L.; Polimeno, A. Mol. Phys. 1996, 88, 315.
42. Braun, D.; Nordio, P.; Polimeno, A.; Saielli, G. Chem. Phys. 1996, 208, 127.
43. Fonseca, T.; Kim, H. J.; Hynes, J. T. J. Mol. Liq. 1994, 161.
44. Fonseca, T.; Kim, H. J.; Hynes, J. T. J. Photochem. Photobiol. A 1994, 82, 67.
45. Kim, H. J.; Hynes, J. T. J. Photochem. Photobiol. A 1997, 105, 337.
46. Gedeck, P.; Schneider, S. J. Photochem. Photobiol. A 1997, 105, 165.
47. Gedeck, P.; Schneider, S. J. Photochem. Photobiol. A 1999, 121, 7.
48. Velapoldi, R.; Mielenz, K. A Fluorescence Standard Reference Material:" Quinine Sulfate Dihydrate; National Bureau of Standards: Washington, DC, 1980; VoL Special Publications 260-64.
49. Heitz, M. P.; Maroncelli, M. J. Phys. Chem. A 1997, 101, 5852.
50. Frisch, M. J.; Trucks, G. W.; Schlegel, H B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi. R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Rega, N.; Salvador, P.; Dannenberg, I. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C. ; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.11.3; Gaussian, Inc.: Pittsburgh, PA, 2002.
51. AMPAC. 6.55 ed.; Semichem Inc.: 7128 Summit, Shawnee, KS 66216, 1999.
52. Klampt, A. J. Phys. Chem. 1995, 99, 2224.
53. Cramer, C. J.; Truhlar, D. G. Chem. Rev. 1999, 99, 2161.
54. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027.
55. Laws, W. R.; Brand, L. J. Phys. Chem. 1979, 83, 795.
56. Marcus, R. A. J. Phys. Chem. 1989, 93, 3078.
57. Koutek, B. Collect. Czech. Chem. Commun. 1978, 43, 2368.
58. Malaga, N.; Kubota, T. Molecular Interactions and Electronic Spectra; Mercel Dekker: New York, 1970.
59. LE〉
60. Van der Auweraer, M.; Grabowski, Z. R.; Rettig, W. J. Phys. Chem. 1991, 95, 2083.
61. Rettig, W.; Bliss, B.; Dirnberger, K. Chem. Phys. Lett. 1999, 305, 8.
62. Schuddenboom, W.; Jonker, S. A.; Warman, J. M.; Leinhos, U.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. 1992, 96, 10809.
63. Druzhinin, S. I.; Demeter, A.; Galievsky, V. A.; Yoshihara, T.; Zachariasse, K. A. J. Phys. Chem. A 2003, 107, 8075.
64. Il'ichev, Y. V.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. A 1998, 102, 5670.
65. Birks, J. B. Photophysics of Aromatic Molecules; Wiley: London, 1970.
66. Lewis, J. E.; Maroncelli, M. Chem. Phys. Lett. 1998, 282, 197.
67. Okada, T.; Uesugi, M.; Köhler, G.; Rechthaler, K.; Rotkiewicz, K.; Rettig, W.; Grabner, G. Chem. Phys. 1999, 247, 327.
68. Dorairaj, S.; Kim, H. J. J. Phys. Chem. A 2002, 106, 2322.
69. van der Zwan, G.; Hynes, J. T. J. Phys. Chem. 1985, 89, 4181.
70. Böttcher, C. J. F.; van Belle, O. C.; Bordewijk, P.; Rip, A. Vol. 1: Theory of Electric Polarization: Dielectrics in Static Fields; Elsevier: Amsterdam, 1973; Vol. I.
71. W. Song and M. Maroncelli, unpublished results of AMI/CI calculations using the COSMO solvation method.
72. Gorse, A.-D.; Pesquer, M. J. Phys. Chem. 1995, 99, 4039.
73. Cave, R.; Newton, M. Chem. Phys. Lett. 1996, 249, 15.
74. 2 to which proper association has been made on the basis of transition moment directions.
75. Bondi, A. J. Phys. Chem. 1964, 68, 441.
76. 94
77. Press, W.; Flannery, B.; Teukolsky, S.; Vetterling, W. Numerical Recipies - The Art of Scientific Computing; Cambridge University Press: Cambridge, 1986.
78. Bevington, P. R. Data Reduction and Error Analysis for the Physical Sciences; McGraw-Hill: New York, 1969.
79. -1.
80. 95 might work belter than a single-cavity approach. However, we find that such an approach worsens the agreement between the model and experiment.
81. This idea is far from new. See for example, the discussion in refs 1, 60, and 96.
82. Koti, A. S. R.; Krishna, M. M. G.; Periasamy, N. J. Phys. Chem. A 2001, 105, 1767.
83. Koti, A. S. R.; Periasamy, N. Res. Chem. Interned. 2002, 28, 831.
84. Chapman, C. F.; Fee, R. S.; Maroncelli, M. J. Phys. Chem. 1995, 99, 4811.
85. Su, S.-G.; Simon, J. D. J. Phys. Chem. 1989, 93, 753.
86. 28
87. Hynes, J. T. The Theory of Reactions in Solution. In The Theory of Chemical Reactions; Baer, M., Csizmadia, I. G., Eds.; CRC Press: Boca Raton, 1985; p 171.
88. Fleming, G. R.; Hanggi, P. Activated Barrier Crossing; World Scientific: Singapore, 1993.
89. -1 is representative.
90. Rettig, W.; Fritz, R.; Braun, D. J. Phys. Chem. A 1997, 101, 6830.
91. Shaik, S. S.; Schlegel, H.; Wolfe, S. Theoretical Aspects of Physical Organic Chemistry; Wiley: New York, 1992.
92. 52 with a solvent radius of 2.6 Å. For ease of calculation the geometry of the solute was maintained at the optimized geometry of the LE minimum and only the twist angle θ varied.
93. Kwok, W. M.; George, M. W.; Grills, D. C; Ma, C.; Mafousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. Angew. Chem., Int. Ed. Engl. 2003, 42, 1826.
94. Brinck, T.; Murray, J. S.; Politzer, P. J. Chem. Phys. 1993, 98, 4305.
95. Basilevsky, M. V.; Rostov, I. V.; Newton, M. D. Chem. Phys. 1998, 232, 189.
96. Rettig, W.; Rotkiewicz, K.; Rubaszewska, W. Spectrochim. Acta 1984, 40A, 241.