Dynamics and efficiency of electron injection and transport in DNA using pyrenecarboxamide as an electron donor and 5-bromouracil as an electron acceptor

Journal of Physical Chemistry B

Volumn 114, Issue 45, 2010, Pages 14265-14272

  Daublain, Pierre ^a   Thazhathveetil, Arun K ^a   Shafirovich, Vladimir ^b   Wang, Qiang ^c   Trifonov, Anton ^c   Fiebig, Torsten ^c   Lewis, Frederick D ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b BOSTON COLLEGE   (United States)

^c NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE COMPOUNDS; CHROMOPHORES; ELECTRON TRANSITIONS; ELECTRON TRANSPORT PROPERTIES; PHOTOCHEMICAL FORMING; QUANTUM CHEMISTRY; QUANTUM YIELD; QUENCHING; RATE CONSTANTS;

BASE PAIRS; CATION-RADICALS; CHARGE SEPARATIONS; ELECTRON ACCEPTOR; ELECTRON DONORS; ELECTRON TRANSPORT; INTERCALATED STRUCTURES; MULTI-STEP; PHOTOCHEMICAL BEHAVIORS; PHOTOPHYSICAL; PYRENE FLUORESCENCE; SINGLE-STEP; SUPEREXCHANGES; TRANSIENT ABSORPTION SPECTRA;

ELECTRON ENERGY LOSS SPECTROSCOPY;

EID: 78650122347     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp9107393     Document Type: Article

References (54)

1. (a) Lewis, F. D. Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3, pp 105-175.
2. (b) Schuster, G. B., Ed. Long-Range Charge Transfer in DNA, I and II; Springer, 2004; Vol. 236, 257.
3. (c) Wagenknecht, H. A. Charge Transfer in DNA; Wiley-VCH: Weinheim, 2005.
4. Seidel, C. A. M.; Schulz, A.; Sauer, M. H. M. J. Phys. Chem. 1996, 100, 5541-5553.
5. (a) Schwogler, A.; Burgdorf, L. T.; Carell, T. Angew. Chem., Int. Ed. 2000, 39, 3918-3920.
6. (b) Breeger, S.; Hennecke, U.; Carell, T. J. Am. Chem. Soc. 2004, 126, 1302-1303.
7. Behrens, C.; Burgdorf, L. T.; Schwogler, A.; Carell, T. Angew. Chem., Int. Ed. 2002, 41, 1763-1766.
8. Giese, B.; Carl, B.; Carl, T.; Carell, T.; Behrens, C.; Hennecke, U.; Schiemann, O.; Feresin, E. Angew. Chem., Int. Ed. 2004, 43, 1848-1851.
9. Carell, T.; Behrens, C.; Gierlich, J. Org. Biomol. Chem. 2003, 7, 2221-2228.
10. Stafforst, T.; Diederichsen, U. Angew. Chem., Int. Ed. 2006, 45, 5376-5380.
11. (a) Ito, T.; Rokita, S. E. J. Am. Chem. Soc. 2003, 125, 11480-11481.
12. (b) Ito, T.; Rokita, S. E. J. Am. Chem. Soc. 2004, 126, 15552-15559.
13. (c) Manetto, A.; Breeger, S.; Chatgilialoglu, C.; Carell, T. Angew. Chem., Int. Ed. 2006, 45, 318-321.
14. Ito, T.; Kondo, A.; Terada, S.; Nishimoto, S. J. Am. Chem. Soc. 2006, 128, 10934-10942.
15. Elias, B.; Shao, F. W.; Barton, J. K. J. Am. Chem. Soc. 2008, 130, 1152-1153.
16. Kawai, K.; Kimura, T.; Kawabata, K.; Tojo, S.; Majima, T. J. Phys. Chem. B 2003, 107, 12838-12841.
17. Daublain, P.; Thazhathveetil, A. K.; Wang, Q.; Trifonov, A.; Fiehig, T.; Lewis, F. D. J. Am. Chem. Soc. 2009, 131, 16790-16797.
18. (a) Kaden, P.; Mayer-Enthart, E.; Trifonov, A.; Fiebig, T.; Wagenknecht, H.-A. Angew. Chem., Int. Ed. 2005, 44, 1636-1639.
19. (b) Gaballah, S. T.; Collier, G.; Netzel, T. L. J. Phys. Chem. B 2005, 109, 12175-12181.
20. Siegmund, K.; Daublain, P.; Wang, Q.; Trifonov, A.; Fiebig, T.; Lewis, F. D. J. Phys. Chem. B 2009, 113, 16276-16284.
21. Lewis, F. D.; Zhu, H.; Daublain, P.; Fiebig, T.; Raytchev, M.; Wang, Q.; Shafirovich, V. J. Am. Chem. Soc. 2006, 128, 791-800.
22. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules, 2nd ed.; Academic Press: New York, 1971.
23. Astruc, D. Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2.
24. Murov, S. L. Handbook of Photochemistry; Marcel Dekker: New York, 1973.
25. Alfred, J.-C.; Daunis, J.; Jacquier, R. Macromol. Chem. Phys. 1996, 197, 389-401.
26. Johnson, W. C. Circular Dichroism, Principles and Applications; Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: New York, 2000; pp 741-768.
27. CAChe CAChe Release 6.1.10, 2000.
28. Raytchev, M.; Pandurski, E.; Buchvarov, I.; Modrakowski, C.; Fiebig, T. J. Phys. Chem. A 2003, 107, 4592-4600.
29. Lewis, F. D.; Daublain, P.; Delos Santos, G.; Liu, W.; Asatryan, A. M.; Markarian, S. A.; Fiebig, T.; Raytchev, M.; Wang, Q. J. Am. Chem. Soc. 2006, 128, 791-800.
30. Gosztola, D.; Niemczyk, M. P.; Svec, W.; Lukas, A. S.; Wasielewski, M. R. J. Phys. Chem. A 2000, 104, 6545-6551.
31. (a) Sugiyama, H.; Tsutsumi, Y.; Saito, I. J. Am. Chem. Soc. 1990, 112, 6720-6721.
32. (b) Fujimoto, K.; Sugiyama, H.; Saito, I. Tetrahedron Lett. 1998, 39, 2137-2140.
33. (a) Shafirovich, V. Y.; Dourandin, A.; Luneva, N. P.; Geacintov, N. E. J. Phys. Chem. B 1997, 101, 5863-5868.
34. (b) Geacintov, N. E.; Solntsev, K.; Johnson, L. W.; Chen, J. X.; Kolbanovskiy, A. D.; Liu, T. M.; Shafirovich, V. Y. J. Phys. Org. Chem. 1998, 11, 561-565.
35. Zahavy, E.; Fox, M. A. J. Phys. Chem. B 1999, 103, 9321-9327.
36. (a) Mann, J. S.; Shibata, Y.; Meehan, T. Bioconjugate Chem. 1992, 5, 554-558.
37. (b) Schuster, G. B. Acc. Chem. Res. 2000, 33, 253-260.
38. (c) Lewis, F. D.; Zhang, L.; Liu, X.; Zuo, X.; Tiede, D. M.; Long, H.; Schatz, G. S. J. Am. Chem. Soc. 2005, 127, 14445-14453.
39. Tuma, J.; Connors, W. H.; Stitelman, D. H.; Richert, C. J. Am. Chem. Soc. 2002, 124, 4236-4246.
40. (a) Siegmund, K.; Maheshwary, S.; Narayanan, S.; Connors, W.; Riedrich, M.; Printz, M.; Richert, C. Nucleic Acids Res. 2005, 33, 4838-4848.
41. (b) Tuma, J.; Paulini, R.; Stütz, J. A. R.; Richert, C. Biochemistry 2004, 43, 15680-15687.
42. Weller, A. Zeit. Phys. Chem. Neue. Folg. 1982, 133, 93-98.
43. (a) Hess, S.; Götz, M.; Davis, W. B.; Michel-Beyerle, M. E. J. Am. Chem. Soc. 2001, 123, 10046-10055.
44. (b) von Feilitzsch, T.; Tuma, J.; Neubauer, H.; Verdier, L.; Haselsberger, R.; Feick, R.; Gurzadyan, G.; Voityuk, A. A.; Griesinger, C.; Michel-Beyerle, M. E. J. Phys. Chem. B 2008, 112, 973-989.
45. Lewis, F. D.; Zhang, L.; Kelley, R. F.; McCamant, D.; Wasielewski, M. R. Tetrahedron 2007, 63, 3457-3464.
46. Valis, L.; Wang, Q.; Raytchev, M.; Buchvarov, I.; Wagenknecht, H. A.; Fiebig, T. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10192-10195.
47. Marcus, R. A. J. Chem, Phys. 1965, 43, 679-701.
48. (a) Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K. J. Am. Chem. Soc. 1995, 117, 6406-6407.
49. (b) Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063-7068.
50. (a) Conwell, E. M.; Basko, D. M. J. Am. Chenu Soc. 2001, 123, 11441-11445.
51. (b) Kurnikov, I. V.; Tong, G. S. M.; Madrid, M.; Beratan, D. N. J. Phys. Chem. B 2002, 106, 7-10.
52. Rivera, E.; Schuler, R. H. J. Phys. Chem. 1983, 87, 3966-3971.
53. Lewis, F. D.; Liu, J.; Zuo, X.; Hayes, R. T.; Wasielewski, M. R. J. Am. Chem. Soc 2003, 125, 4850-4861.
54. Lewis, F. D.; Liu, J.; Weigel, W.; Rettig, W.; Kurnikov, I. V.; Beratan, D. N. Proc Natl. Acad. Sci. U.S.A. 2002, 99, 12536-12541.