Photoinduced electron transfer in self-assembled dimers of 3-fold symmetric donor-acceptor molecules based on perylene-3,4:9,10-bis(dicarboximide)

Journal of Physical Chemistry A

Volumn 108, Issue 37, 2004, Pages 7497-7505

  Rybtchinski, Boris ^a   Sinks, Louise E ^a   Wasielewski, Michael R ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DONORS; EXCITED STATES; FEMTOSECOND TRANSIENT ABSORPTION SPECTROSCOPY; SOLVOPHOBIC INTERACTIONS;

DIMERS; ELECTRON TRANSITIONS; FREE RADICALS; IONS; MONOMERS; PHOTOCHEMICAL REACTIONS; SELF ASSEMBLY;

AROMATIC COMPOUNDS;

EID: 4644250339     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp048883u     Document Type: Article

References (68)

1. Balzani, V.; Scandola, F. Supramolecular photochemistry; Ellis Horwood: New York, 1991.
2. Turro, N. J. J. Photochem. Photobiol. A 1996, 100, 53-56.
3. Armaroli, N. Photochem. Photobiol. Sci. 2003, 2, 73-87.
4. Gloss, G. L.; Miller, J. R. Science 1988, 240, 440-447.
5. Paddon-Row, M. Aust. J. Chem. 2003, 56, 729-748.
6. Meyer, T. J. Acc. Chem. Res. 1989, 22, 163-170.
7. Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
8. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40-48.
9. Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 55, 57-69.
10. Aratani, N.; Osuka, A.; Chob, H. S.; Kim, D. J. Photochem. Photobiol. C 2002, 3, 25-52.
11. Imahori, H.; Mori, Y.; Matano, Y. J. Photochem. Photobiol. C 2003, 4, 51-83.
12. Shimomura, M.; Karthaus, O.; Ijiro, K. Synth Met. 1996, 81, 251-257.
13. Dinolfo, P. H.; Hupp, J. T. Chem. Mater. 2001, 13, 3113-3125.
14. Reinhoudt, D. N.; Crego-Calama, M. Science 2002, 295, 2403-2407.
15. Kaschak, D. M.; Johnson, S. A.; Waraksa, C. C.; Pogue, J.; Mallouk, T. E. Coord. Chem. Rev. 1999, 185-186, 403-416.
16. Kobuke, Y.; Ogawa, K. Bull. Chem. Soc. Jpn. 2003, 76, 689-708.
17. Hwang, I.-W.; Cho, H. S.; Jeong, D. H.; Kim, D.; Tsuda, A.; Nakamura, T. ; Osuka, A. J. Phys. Chem. B 2003, 107, 9977-9988.
18. Pope, M.; Swenberg, C. E. Electronic Processes in Organic Crystals and Polymers, 2nd ed.; Oxford University Press: New York, 1999.
19. Würthner, F. Angew. Chem., Int. Ed. 2001, 40, 1037-1039.
20. Anthony, J. E.; Eaton, D. L.; Parkin, S. R. Org. Lett. 2002, 4, 15-18.
21. Sheraw, C. D.; Jackson, T. N.; Eaton, D. L.; Anthony, J. E. Adv. Mater. 2003, 15, 2009-2011.
22. Kazmaier, P. M.; Hoffmann, R. H. J. Am. Chem. Soc. 1994, 116, 9684-9691.
23. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
24. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin. Trans. 2001, 651-669.
25. Waters, M. L. Curr. Opin. Chem. Biol. 2002, 6, 736-741.
26. Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807-818.
27. Sui, G.; Orbulescu, J.; Mabrouki, M.; Leblanc, R. M.; Liu, S.; Gregg, B. A. ChemPhysChem 2002, 12, 1041-1044.
28. Sui, G.; Orbulescu, J.; Mabrouki, M.; Micic, M.; Leblanc, R. M.; Liu, S. ; Cormier, R. A.; Gregg, B. A. J. Phys. Chem. B 2002, 106, 9335-9340.
29. Liu, S.-G.; Sui, G.; Cormier, R. A.; Leblanc, R. M.; Gregg, B. A. J. Phys. Chem. B 2002, 106, 1307-1315.
30. Würthner, F.; Thalacker, C.; Sautter, A.; Schartel, W.; Ibach, W.; Hollricher, O. Chem. Eur. J. 2000, 6, 3871-3886.
31. Sautter, A.; Thalacker, C.; Heise, B.; Würthner, F. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4993-4996.
32. Schmidt-Mende, L.; Fechtenkotter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1122.
33. Schenning, A. P. H. J.; Herrikhuyzen, J. v.; Jonkheijm, P.; Chen, Z.; Würthner, F.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 10252-10253.
34. Peumans, P.; Uchida, S.; Forrest, S. R. Nature 2003, 425, 158-162.
35. Li, A. D. Q.; Wang, W.; Wang, L.-Q. Chem. Eur. J. 2003, 9, 4594-4601.
36. Wang, W.; Han, J. J.; Wang, L.-Q.; Li, L.-S.; Shaw, W. J.; Li, A. D. Q. Nano Lett. 2003, 3, 455-458.
37. Wang, W.; Li, L.-S.; Helms, G.; Zhou, H.-H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120-1121.
38. Wang, W.; Wan, W.; Zhou, H.-H.; Niu, S.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 5248-5249.
39. Gregg, B. A. J. Phys. Chem. B 2003, 107, 4688-4698.
40. van der Boom, T.; Hayes, R. T.; Zhao, Y.; Bushard, P. J.; Weiss, E. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2002, 124, 9582-9590.
41. Asaki, M. T.; Huand, C.-P.; Garvey, D.; Zhou, J.; Kapteyn, H.; Murnane, M. M. Opt. Lett. 1993, 18, 977-979.
42. Lukas, A. S.; Miller, S. E.; Wasielewski, M. R. J. Phys. Chem. B 2000, 104, 931-940.
43. Greenfield, S. R.; Wasielewski, M. R. Opt. Lett. 1995, 20, 1394-1396.
44. Greenfield, S. R.; Wasielewski, M. R. Appl. Opt. 1995, 34, 2688-2691.
45. Giaimo, J. M.; Gusev, A. V.; Wasielewski, M. R. J. Am. Chem. Soc. 2002, 124, 8530-8531.
46. Zang, L.; Liu, R.; Holman, M. W.; Nguyen, K. T.; Adams, D. M. J. Am. Chem. Soc. 2002, 124, 10640-10641.
47. He, J.; Machida, S.; Kishi, H.; Horie, K.; Furukawa, H.; Yokota, R. J. Polym. Sci. A 2002, 40, 2501-2512.
48. Kasha, M.; Rawles, H. R.; El-Bayoumi, M. A. Pure Appl. Chem 1965, 11, 371-392.
49. Langhals, H.; Jona, W. Angew. Chem., Int. Ed. Engl. 1998, 37, 952-955.
50. Langhals, H.; Ismael, R. Eur. J. Org. Chem. 1998, 1915-1917.
51. Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem. Eur. J. 2001, 7, 2245-2253.
52. Saiki, Y.; Sugiura, H.; Nakamura, K.; Yamaguchi, M.; Hoshi, T.; Anzai, J. J. Am. Chem. Soc. 2003, 125, 9268-9269.
53. Wu, J.; Watson, M. D.; Müllen, K. Angew. Chem., Int. Ed. 2003, 42, 5329-5333.
54. HyperChem; Hypercube, Inc.: 1115 NW 1114th Street, Gainesville, FL 32601.
55. Castonguay, L. A.; Rappe, A. K.; Casewit, C. J. J. Am. Chem. Soc. 1991, 113, 7177-7183.
56. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Kenneth, M.; Merz, J.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5197.
57. Hobza, P.; Kavelac, M.; Sponer, J.; Mejzlic, P.; Vondrasek, J. J. Comput. Chem. 1997, 18, 1136-1150.
58. Piosik, J.; Zdunek, M.; Kapuscinski, J. Biochem. Pharmacol. 2002, 63, 635-646.
59. Fry, A. F. Synthetic Organic Electrochemistry, Harper & Row: New York, 1972.
60. Greenfield, S. R.; Svec, W. A.; Gosztola, D.; Wasielewski, M. R. J. Am. Chem. Soc. 1996, 118, 6767-6777.
61. Weller, A. Z. Phys. Chem. 1982, 133, 93-98.
62. Gosztola, D.; Niemczyk, M. P.; Svec, W.; Lukas, A. S.; Wasielewski, M. R. J. Phys. Chem. A 2000, 104, 6545-6551.
63. Lukas, A. S.; Zhao, Y.; Miller, S. E.; Wasielewski, M. R. J. Phys. Chem. B 2002, 106, 1299-1306.
64. Saigusa, H.; Lim, E. C. Acc. Chem. Res. 1996, 29, 171-178.
65. Goldschmidt, C. R.; Ottolenghi, M. J. Phys. Chem. 1970, 74, 2041.
66. Katoh, R.; Sinha, S.; Murata, S.; Tachiya, M. J. Photochem. Photobiol. A 2001, 145, 23-34.
67. Kochi, J. K.; Rathore, R.; Magueres, P. L. J. Org. Chem. 2000, 65, 6826-6836.
68. Ganesan, V.; Rosokha, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2003, 125, 2559-2571.