Conformationally gated switching between superexchange and hopping within oligo-p-phenylene-based molecular wires

Journal of the American Chemical Society

Volumn 127, Issue 33, 2005, Pages 11842-11850

  Weiss, Emily A ^a   Tauber, Michael J ^a   Kelley, Richard F ^a   Ahrens, Michael J ^a   Ratner, Mark A ^a   Wasielewski, Michael R ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; MAGNETIC FIELD EFFECTS; SWITCHING SYSTEMS; THERMAL EFFECTS;

CHARGE RECOMBINATION (CR); CONFORMATIONALLY GATED SWITCHING; DONOR-BRIDGE-ACCEPTOR (D-B-A) SYSTEMS; PHENOTHIAZINE (PTZ);

CONFORMATIONS;

OLIGO 4 PHENYLENE; PERYLENE; PERYLENE 3,4,9,10 BIS(DICARBOXIMIDE); PHENOTHIAZINE DERIVATIVE; PHENYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHARGE RECOMBINATION; CONFORMATION; EQUILIBRIUM CONSTANT; MAGNETIC FIELD; MATHEMATICAL ANALYSIS; MOLECULAR DYNAMICS; PREDICTION; PRODUCT RECOVERY; SURFACE CHARGE; TEMPERATURE DEPENDENCE; THERMAL ANALYSIS; TRANSPORT KINETICS;

CRYSTALLOGRAPHY, X-RAY; MAGNETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PERYLENE; TEMPERATURE;

EID: 23944477885     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052901j     Document Type: Article

References (91)

1. Deisenhofer, J.; Epp, O.; Miki, K.; Huber, R.; Michel, H. J. Mol. Biol. 1984, 180, 385.
2. Fromme, P.; Kern, J.; Loll, B.; Biesiadka, J.; Saenger, W.; Witt, H. T.; Krauss, N.; Zouni, A. Philos. Trans. R. Soc. London, B 2002, 357, 1337.
3. Witt, H. T. Adv. Photosynth. 1996, 4, 363.
4. Bixon, M.; Jortner, J. Adv. Chem. Phys. 1999, 106, 35.
5. Jortner, J.; Bixon, M.; Langenbacher, T.; Michel-Beyerle, M. E. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12759.
6. Berlin, Y. A.; Burin, A. L.; Ratner, M. A. Chem. Phys. 2002, 275, 61.
7. Berlin, Y. A.; Burin, A. L.; Ratner, M. A. J. Phys. Chem. A 2000, 104, 443.
8. Berlin, Y. A.; Hutchison, G. R.; Rempala, P.; Ratner, M. A.; Michl, J. J. Phys. Chem. A 2003, 107, 3970.
9. Troisi, A.; Ratner, M. A.; Nitzan, A. J. Chem. Phys. 2003, 118, 6072.
10. Segal, D.; Nitzan, A.; Davis, W. B.; Wasielewski, M. R.; Ratner, M. A. J. Phys. Chem. B 2000, 104, 3817.
11. Segal, D.; Nitzan, A.; Ratner, M. A.; Davis, W. B. J. Phys. Chem. B 2000, 104, 2790.
12. Paulson, B. P.; Miller, J. R.; Gan, W.-X.; Closs, G. L. J. Am. Chem. Soc. 2005, 127, 4860.
13. Weiss, E. A.; Ahrens, M. J.; Sinks, L. E.; Rainer, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 5577.
14. Weiss, E. A.; Ahrens, M. J.; Sinks, L. E.; Rainer, M. A.; Wasielewski, M. A. J. Am. Chem. Soc. 2004, 126, 9510.
15. 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.
16. Meerholz, K.; Heinze, J. Electrochim. Acta 1996, 41, 1839.
17. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265.
18. Lukas, A. S.; Bushard, P. J.; Weiss, E. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2003, 125, 3921.
19. Weiss, E. A.; Ratner, M. A.; Wasielewski, M. R. J. Phys. Chem. A 2003, 107, 3639.
20. Szymoszek, A.; Koll, A. Chem. Phys. Lett. 2000, 324, 115.
21. McCreery, R. L.; Anariba, F. J. Phys. Chem. B 2002, 106, 10355.
22. Marcus, R. A. Chem. Phys. Lett. 1987, 133, 471.
23. Ogrodnik, A.; Michel-Beyerle, M.-E. Z. Naturforsch. 1989, 44a, 763.
24. Lukas, A. S.; Bushard, P. J.; Wasielewski, M. R. J. Phys. Chem. A 2002, 106, 2074.
25. Kilsa, K.; Kajanus, J.; Macpherson, A. N.; Martensson, J.; Albisson, B. J. Am. Chem. Soc. 2001, 123, 3069.
26. Kramers, H. A. Physica 1934, 1, 182.
27. Anderson, P. W. Phys. Rev. 1959, 115, 2.
28. Anderson, P. W. Phys. Rev. 1950, 79, 350.
29. Weiss, E. A.; Sinks, L. E.; Lukas, A. S.; Chernick, E. T.; Wasielewski, M. R. J. Phys. Chem. B 2004, 108, 10309.
30. Kobori, Y.; Sekiguchi, S.; Akiyama, K.; Tero-Kubota, S. J. Phys. Chem. A 1999, 103, 5416.
31. Paddon-Row, M. N.; Shephard, M. J. J. Phys. Chem. A 2002, 106, 2935-2944.
32. Volk, M.; Haberle, T.; Feick, R.; Ogrodnik, A.; Michel-Beyerle, M. E. J. Phys. Chem. 1993, 97, 9831.
33. Closs, G. L.; Miller, J. R. Science 1988, 240, 440.
34. Yamashita, J.; Kondo, J. Phys. Rev. 1958, 109, 730.
35. Kramers, H. A. Physica 1934, 1.
36. Gloss, G. L.; Miller, J. R. Science 1988, 240, 440.
37. Feher, G., Okamura, M., Eds. Tunneling In Biological Systems; Academic Press: New York, 1979.
38. Weller, A.; Staerk, H.; Treichel, R. Chem. Soc. Faraday Discuss. 1984, 78, 271.
39. Volk, M.; Haberle, T.; Feick, R.; Ogrodnik, A.; Michel-Beyerle, M.-E. J. Phys. Chem. 1993, 97, 9831.
40. Till, U.; Hore, P. J. Mol. Phys. 1997, 90, 289.
41. Steiner, U. E.; Ulrich, T. Chem. Rev. 1989, 89, 51.
42. Tanimoto, Y.; Okada, N.; Itoh, M.; Iwai, K.; Sugioka, K.; Takemura, F.; Nakagaki, R.; Nagakura, S. Chem. Phys. Lett. 1987, 136, 42.
43. Schulten, K.; Staerk, H.; Weller, A.; Werner, H.; Nickel, B. Z. Phys. Chem. NF 1976, 101, 371.
44. Werner, U.; Kuhnle, W.; Staerk, H. J. Phys. Chem. 1993, 97, 9280.
45. Shultz, D. A.; Fico, R. M.; Lee, H.; Kampf, J. W.; Kirschbaum, K.; Pinkerton, A. A.; Boyle, P. D. J. Am. Chem. Soc. 2003, 125, 15426.
46. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
47. Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
48. Jaguar 3.5; Schrodinger, Inc.: Portland, Oregon, 1998.
49. Daub, J.; Engl, R.; Kurzawa, J.; Miller, S. E.; Schneider, S.; Stockmann, A.; Wasielewski, M. R. J. Phys. Chem. A 2001, 105, 5655.
50. Heimel, G.; Daghofer, M.; Gierschner, J.; List, E. J. W.; Grimsdale, A. C.; Mullen, K.; Belijonne, D.; Bredas, J.-L.; Zojer, E. J. Chem. Phys. 2005, 122, 054501.
51. Cacelli, I.; Prampolini, G. J. Phys. Chem. A 2003, 107, 8665.
52. Honda, K.; Furukawa, Y. J. Mol. Struct. 2005, 735-736, 11.
53. HyperChem; Hypercube, Inc.; 1115 NW 4th Street. Gainesville, FL 32601, USA.
54. Weller, A. Z. Phys. Chem. 1982, 133, 93.
55. Weiss, E. A.; Tauber, M. J.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2005, 127, 6052.
56. Osuka, A.; Maruyama, K.; Mataga, N.; Asahi, T.; Yamazaki, I.; Tamai, N. J. Am. Chem. Soc. 1990, 112, 2.
57. Helms, A.; Heiler, D.; McClendon, G. J. Am. Chem. Soc. 1992, 114, 6227.
58. Kim, Y.; Lieber, C. M. Inorg. Chem. 1989, 28, 3990.
59. Helms, A.; Heiler, D.; McClendon, G. J. Am. Chem. Soc. 1991, 113, 4325.
60. Osuka, A.; Satoshi, N.; Maruyama, K.; Mataga, N.; Asahi, T.; Yamazaki, I.; Nishimura, Y.; Onho, T.; Nozaki, K. J. Am. Chem. Soc. 1993, 115, 4577.
61. Barigelletti, F.; Flamigni, L.; Balzani, V.; Collin, J.-P.; Sauvage, J.-P.; Sour, A.; Constable, E. C.; Cargill Thompson, A. M. W. J. Am. Chem. Soc. 1994, 116, 7692.
62. Barigelletti, F.; Flamigni, L.; Guardgli, M.; Juris, A.; Beley, M.; Chodor-owsky-Kimmes, S.; Collin, J.-P.; Sauvage, J.-P. Inorg. Chem. 1996, 35, 136.
63. Marcus, R. A. J. Chem. Phys. 1965, 43, 679.
64. Goller, A.; Grummt, U.-W. Chem. Phys. Lett. 2000, 321, 399.
65. Grein, F. Theor. Chem. Acc. 2003, 109, 274.
66. Moliton, A.; Hiorns, R. C. Polym. Int. 2004, 53, 1397.
67. Bredas, J.-L.; Chance, B.; Silbey, R. Phys. Rev. B 1982, 26, 5843.
68. Tsuzuki, S.; Uehimaru, T.; Matsumura, K.; Mikami, M.; Tanabe, K. J. Chem. Phys. 1999, 110, 2858.
69. Pan, J.-F.; Chua, S.-J.; Huang, W. Thin Solid Films 2000, 363, 1.
70. Weiss, E. A.; Ahrens, M. J.; Sinks, L. E.; Gusev, A. V.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 5577.
71. Davis, W. B.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2001, 123, 7877.
72. Kiselev, V. D.; Miller, J. R. J. Am. Chem. Soc. 1975, 97, 4036.
73. Zaman, K. M.; Yamamoto, S.; Nishimura, N. J. Am. Chem. Soc. 1994, 116, 12099.
74. Yamamoto, S.; Sakurai, T.; Yingjin, L.; Sueishi, Y. Phys. Chem. Chem. Phys. 1999, 1, 833.
75. Fukuzumi, S.; Ohkubo, K.; Tokuda, Y.; Suenobu, T. J. Am. Chem. Soc. 2000, 122, 4286.
76. Frank, R.; Greiner, G.; Rau, H. Phys. Chem. Chem. Phys. 1999, 1, 3841.
77. Steinfeld, J. I.; Francisco, J. S.; Hase, W. L. Chemical Kinetics and Dynamics, 2nd ed.; Prentice Hall, Inc.: Upper Saddle River, NJ, 1999.
78. Berlin, Y. A.; Burin, A. L.; Ratner, M. A. Chem. Phys. 2002, 275, 61.
79. Blankenship, R. E. Acc. Chem. Res. 1981, 14, 163.
80. DFT is considered a reliable technique for studying energy barriers and conjugation in oligophenylenes, and DFT calculations with a moderate basis set agree with MP2 calculations using an extensive cc-pVQZ basis set for biphenyl.
81. Tkaczyk, S. W. Proc. SPIE-Int. Soc. Opt. Eng. 2001, 4413, 226.
82. Melzer, P.; Kurreck, H.; Kieslich, W. Chem. Bur. 1982, 115, 3597.
83. Tekely, P.; Laupretre, F.; Monnerie, L. Macromolecules 1983, 16, 415.
84. Scherer, P. O. J.; Fischer, F. Chem. Phys. Lett. 1987, 141, 179.
85. Vauthey, E.; Suppan, P. Chem. Phys. 1989, 139, 381.
86. Woodbury, N. W.; Becker, M.; Middendorf, D.; Parson, W. W. Biochemistry 1985, 24, 7516.
87. Bixon, M.; Jortner, J. J. Phys. Chem. 1991, 95, 1941.
88. Buhks, E.; Jortner, J. FEBS Lett. 1980, 109, 117.
89. Mitsui, M. J. Chem. Phys. 2002, 117, 9740.
90. Parson, W. W. Biochim. Biophys. Acta 1967, 131, 154.
91. Pan, D.; Phillips, D. L. J. Phys. Chem. A 1999, 103, 4737.