Solvatochromism of distyrylbenzene pairs bound together by [2.2]paracyclophane: Evidence for a polarizable "through-space" delocalized state

Journal of the American Chemical Society

Volumn 127, Issue 20, 2005, Pages 7435-7443

  Hong, Janice W ^a   Woo, Han Young ^a   Liu, Bin ^a   Bazan, Guillermo C ^a  

^a Santa Barbara   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CHEMICAL BONDS; CHROMOPHORES; FLUORESCENCE; SOLVENTS;

DISTRYLBENZENE; EXCITED STATES; POLAR SOLVENTS; RED-SHIFT;

BENZENE;

BENZENE DERIVATIVE; CYCLOPHANE DERIVATIVE; DISTYRYLBENZENE; UNCLASSIFIED DRUG;

ARTICLE; BASE PAIRING; CHROMATOPHORE; COMPLEX FORMATION; COVALENT BOND; DIMERIZATION; DNA DAMAGE; POLARIZATION; SEMICONDUCTOR; SOLVATION; STEADY STATE; SYNTHESIS;

EID: 19744365931     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044326+     Document Type: Article

References (125)

1. (a) Clayton, R. K. Photosynthesis: Physical Mechanisms and Chemical Patterns; Cambridge University Press: New York, 1980.
2. (b) Hu, X.; Damjanovíc, A.; Ritz, T.; Schulten, K. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 5935.
3. (c) Sundström, V.; van Grondelle, R. In Anoxygenic Pholosynthetic Bacteria; Blankenship, R. E., Madigan, M. T., Bauer, C. E., Eds.; Kluwer Academic: Boston, MA, 1995.
4. (d) van Grondelle, R.; Dekker: J. P.; Gillbro, T.; Sundström, V. Biochim. Biophys. Acta 1994, 1187, 1.
5. (a) Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R.; Wasielewski, M. R. Science 1997, 277, 673.
6. (b) Armitage, B. Chem. Rev. 1998, 98, 1171.
7. (c) Meggers, E.; Michel-Beyerle, M. E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 12950.
8. (d) Lewis, F. D.; Wu, T.; Liu, X.; Letsinger, R. L.; Greenfield, S. R.; Miller, S. E.; Wasielewski, M. R. J. Am Chem. Soc. 2000, 122, 2889.
9. (e) Lewis, F. D.; Liu, X.; Liu, J.; Miller, S. E.; Hayes, R. T.; Wasielewski, M. R. Nature 2000, 406, 51.
10. (f) Takada, T.; Kawai, K.; Tojo, S.; Majima, T. J. Phys. Chem. B 2004, 108, 761.
11. (g) Takada, T.; Kawai, K.; Cai, X.; Sugimoto, A.; Fujitsuka, M.; Majima, T. J. Am. Chem. Soc. 2004, 126, 1125.
12. (a) Schuster, G. B. Acc. Chem. Res. 2000, 33, 253.
13. (b) Beralan, D. N.; Priyadarshy, S.; Risser, S. M. Chem. Biol. 1997, 4, 3.
14. (c) Turro, N. J.; Barton, J. K. J. Biol. Inorg. Chem. 1998, 3, 201.
15. (d) Henderson, P. T.; Jones, D.; Hampikian, G.; Kan, Y.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 8353.
16. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Kluwer Academic/Plenum Publishers: New York, 1999.
17. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537.
18. Guillet, J. Polymer Photophysics and Photochemistry; Cambridge University Press: Cambridge, U.K., 1985.
19. For a recent review see: Schwartz, B. J. Annu. Rev. Phys. Chem. 2003, 54, 141.
20. Bazan, G. C.; Miao, Y.-J.; Renak, M. L.; Sun, B. J. J. Am. Chem. Soc. 1996, 118, 2618.
21. (a) Varnavski, O. P.; Ostrowski, J. C.; Sukhomlinova, L.; Twieg, R. J.; Bazan, G. C.; Goodson, T. J. Am. Chem. Soc. 2002, 124, 1736.
22. (b) Kumar, P.; Lee, T.-H.; Mehta, A.; Sumpter, B. G.; Dickson, R. M.; Barnes, M. D. J. Am. Chem. Soc. 2004, 126, 3376.
23. (a) Garnier, F. Acc. Chem. Res. 1999, 32, 209.
24. (b) Servet, B.; Horowitz, G.; Ries, S.; Lagorsse, O.; Alnot, P.; Yassar, A.; Deloffre, F.; Srivastava, P.; Hajlaoui, R.; Lang, P.; Garnier, F. Chem. Mater. 1994, 6, 1809.
25. (c) Dodabalapur, A.; Torsi, L.; Katz, H. E. Science 1995, 268, 270.
26. Catalán, J.; Zimányi, L.; Saltiel, J. J. Am. Chem. Soc. 2000, 122, 2377.
27. (a) Saigusa, H.; Lim, E. C. Acc. Chem. Res. 1996, 29, 171.
28. (b) Kim, K. S.; Tarakeshwar, P.; Lee, J. Y. Chem. Rev. 2000, 100, 4145.
29. (a) Jelley, E. E. Nature 1937, 139, 631.
30. (b) Scheibe, G. Angew. Chem. 1937, 50, 212.
31. Siddiqui, S.; Spano, F. C. Chem. Phys. Lett. 1999, 308, 99.
32. Chowdhury, A.; Wachsmann-Hogiu, S.; Bangal, P. R.; Raheem, I.; Peteanu, L. A. J. Phys. Chem. B 2001, 105, 12196.
33. Cornil, J.; dos Santos, D. A.; Crispin, X.; Silbey, R.; Brédas, J.-L. J. Am. Chem. Soc. 1998, 120, 1289.
34. (a) Brédas, J.-L.; Cornil, J.; Beljonne, D.; dos Santos, D. A.; Shuai, Z. G. Acc. Chem. Res. 1999, 32, 267.
35. (b) Tretiak, S.; Mukamel. S. Chem. Rev. 2002, 102, 3171.
36. (c) Spano, F. C. J. Chem. Phys. 2003, 118, 981.
37. (d) Iozzi, M. F.; Mennucci, B.; Tomasi, J.; Cammi, R. J. Chem. Phys. 2004, 120, 7029.
38. (e) Thompson, A. L.; Gaab, K. M.; Xu, J.; Bardeen, C. J.; Martinez, T. J. J. Phys. Chem. A 2004, 108, 671.
39. (a) Nakahara, H.; Fukuda, K.; Möbius, D.; Kuhn, H. J. Phys. Chem. 1986, 90, 6144.
40. (b) Evans, C. E.; Bohn, P. W. J. Am. Chem. Soc. 1993, 115, 3306.
41. (c) Whitten, D. G. Acc. Chem. Res. 1993, 26, 502.
42. (d) Huang, Y.; Cheng, T.; Li, F.; Huang, C-H.; Hou, T.; Yu, A.; Zhao, X.; Xu, X. J. Phys. Chem. B 2002, 106, 10020.
43. Würthner, F.; Yao, S.; Debaerdemaeker, T.; Wortmann, R. J. Am. Chem. Soc. 2002, 124, 9431.
44. (a) Letsinger, R. L.; Wu, T. J, Am. Chem. Soc. 1995, 117, 7323.
45. (b) Lewis, F. D.; Wu, T.; Burch, E. L.; Bassani, D. M.; Yang, J.-S.; Schneider, S.; Jäger, W.; Letsinger, R. L. J. Am. Chem. Soc. 1995, 117, 8785.
46. (c) Lewis, F. D.; Yang, J.-S.; Stern, C. L. J. Am. Chem. Soc. 1996, 118, 2772.
47. Song, X.; Geiger, C.; Furman, I.; Whitten, D. G. J. Am. Chem. Soc. 1994, 116, 4103.
48. Berberan-Santos, M. N.; Choppinet, P.; Fedorov, A.; Jullien, L.; Valeur, B. J. Am. Chem. Soc. 1999, 121, 2526.
49. Scholes, G. D.; Ghiggino, K. P.; Oliver, A. M.; Paddon-Row, M. N. J. Am. Chem. Soc. 1993, 115, 4345.
50. We define "through-space" interactions as perturbations in molecular electronic structure caused by another chromophore via Dexter and/or Förster mechanism(s). See: (a) Gilbert, A.; Baggott, J. Essentials of Molecular Photochemistry; CRC Press: Boca Raton, FL, 1991.
51. (b) Pope, M.; Swenberg, C. E. Electronic Processes in Organic Crystals; Clarendon Press: New York, 1982.
52. (a) Vögtle, F. Cyclophane Chemistry; J. Wiley & Sons: Chichester, England, 1993.
53. (b) Modem Cyclophane Chemistry; Gleiter, R., Hopf, H., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
54. (a) Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Interscience: London, U.K., 1970.
55. (b) Canuto, S.; Zerner, M. C. J. Am. Chem. Soc. 1990, 112, 2114.
56. (c) Iwata, S.; Fuke, K.; Sasaki, M.; Nagakura, S.; Otsubo, T.; Misumi, S. J. Mol. Spectrosc. 1973, 46, 1.
57. Chromophores studied in this manner include the following, (a) Phenanthrenophane: Schweitzer, D.; Hausser, K. H.; Haenel, M. W. Chem. Phys. 1978, 29, 181.
58. (b) Anthracenophane: Ishikawa, S.; Nakamura, J.; Iwata, S.; Sumitani, M.; Nagakura, S.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1346.
59. (c) Fluorenophane: Haenel, M. W. Tetrahedron Lett. 1976. 17, 3121.
60. (d) Colpa, J. P.; Hausser K. H.; Schweitzer, D. Chem. Phys. 1978, 29, 187.
61. (e) Pyrenophane and several isomers of naphthalenophane: Haenel, M.; Staab, H. A. Chem. Ber. 1973, 106, 2203.
62. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858.
63. (f) Stilbenophanes: Anger, I.; Sandros, K.; Sundahl, M.; Wennerström, O. J. Phys. Chem. 1993, 97, 1920.
64. Tsuge, A.; Nishimoto, T.; Uchida, T.; Yasutake, M.; Moriguchi, T.; Sakata, K. J. Org. Chem. 1999, 64, 7246.
65. Cinnamophanes: Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J. P.; Bouas-Laurent H. J. Chem. Soc., Chem. Commun. 1994, 9, 1075.
66. (a) Bartholomew, G. P.; Bazan, G. C. Acc. Chem. Res. 2001, 34, 30.
67. (b) Oldham, W. J.; Miao, Y.-J.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1998, 120, 419.
68. (c) Bazan, G. C.; Oldham, W. J.; Lachicotte, R. J.; Tretiak, S.; Chernyak, V.; Mukamel, S. J. Am. Chem. Soc. 1998, 120, 9188.
69. (a) Wang, S. J.; Bazan, G. C.; Tretiak, S.; Mukamel, S. J. Am. Chem. Soc. 2000. 112, 1289.
70. (b) Verdal, N.; Godbout, J. T.; Perkins, T. L.; Bartholomew, G. P.; Bazan, G. C.; Kelley, A. M. Chem. Phys. Lett. 2000, 320, 95.
71. Zyss, J.; Ledoux, I.; Volkov, S.; Chernyak, V.; Mukamel, S.; Bartholomew, G. P.; Bazan, G. C. J. Am. Chem. Soc. 2000, 122, 11956.
72. (a) Staab, H. A.; Rebafka, W. Chem. Ber. 1977, 110, 3333.
73. (b) Staab, H. A.; Haffner, H. Chem. Ber. 1977, 110, 3358.
74. (c) Staab, H. A.; Starker, B.; Krieger, C. Chem. Ber. 1983, 116, 3831.
75. (d) Staab, H. A.; Schanne, L.; Krieger, C.; Taglieber, V. Chem. Ber. 1985, 118, 1204.
76. (e) Tashiro, M. Koya, K.; Yamato, T. J. Am. Chem. Soc. 1983, 105, 6650.
77. (f) Machida, H.; Tatemitsu, H.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1978, 19, 915.
78. (g) Review: Keehn, P. M. In Cyclophanes; Keehn, P. M., Rosenfeld, S. M., Eds.; Academic Press: New York, 1983.
79. (h) Review: Schwartz, M. H. J. Indus. Phenom. Mol. Rec. Chem. 1990, 9, 1.
80. Sankararaman, S.; Hopf, H.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2000, 15, 2699.
81. (a) Bartholomew, G. P.; Bazan, G. C. J. Am. Chem. Soc. 2002, 124, 5183.
82. (b) Bartholomew, G. P.; Ledoux, I.; Mukamel, S.; Bazan, G. C.; Zyss, J. J. Am. Chem. Soc. 2002, 124, 13480.
83. (a) Wigner, E. P. Group Theory and its Application to the Quantum Mechanics of Atomic Spectra; Academic Press: New York, 1959.
84. (b) Zyss, J. J. Chem. Phys. 1993, 98, 6583.
85. (c) Zyss, J.; Ledoux, I. Chem. Rev. 1994, 94, 77.
86. (d) Joffre, M.; Yaron, D.; Silbey, R. J.; Zyss, J. J. Chem. Phys. 1992, 97, 5607.
87. (e) Cho, M.; An, S.-Y.; Lee, H.; Ledoux, I.; Zyss, J. J. Chem. Phys. 2002, 116, 9165.
88. (a) Morisaki, Y.; Chujo, Y. Macromolecules 2002, 35, 587.
89. (b) Morisaki, Y.; Chujo, Y. Chem. Lett. 2002, 57, 194.
90. (c) Morisaki, Y.; Ishida, T.; Chujo, Y. Macromolecules 2002, 55, 7872.
91. (d) Morisaki, Y.; Ishida, T.; Chujo, Y. Polym. J. 2003, 55, 501.
92. (e) Morisaki, Y.; Fujimura, F.; Chujo, Y. Organometallics 2003, 22, 3553.
93. (f) Morisaki, Y.; Chujo, Y. Macromolecules 2004, 37, 4099.
94. (g) Morisaki, Y.; Chujo, Y. Macromolecules 2003, 56, 9319.
95. (h) Salhi, F.; Collard, D. M. Adv. Mater. 2003, 15, 81.
96. (i) Guyard, L.; An, M. N. D.; Audebert, P. Adv. Mater. 2001, 75, 133.
97. (j) Kaikawa, T.; Takimiya, K.; Aso, Y.; Otsubo, T. Org. Lett. 2000, 2, 4197.
98. (k) Wang, W.; Xu, J.; Lai, Y.-H. Org. Lett. 2003, 5, 2765.
99. Chen, L.; McBranch, D. W.; Wang, H.-L.; Helgeson, R.; Wudl, F.; Whitten, D. G. Proc. Natl. Acad. Sci. 1999, 96, 12287.
100. (a) Hong, J. W.; Gaylord, B. S.; Bazan, G. C. J. Am. Chem. Soc. 2002, 124, 11868.
101. (b) Hong, J. W.; Benmansour, H.; Bazan, G. C. Chem. Eur. J. 2003, 9, 3186.
102. (a) Henderson, K.; Dalton, A. B.; Chambers, G.; Drury, A.; Maier, S.; Ryder, A. G.; Blau, W.; Byrne, H. J. Synth. Met. 2001, 119, 555.
103. (b) Marri, E.; Pannacci, D.; Galiazzo, G.; Mazzucato, U.; Spalletti, A. J. Phys. Chem. A 2003, 107, 11231.
104. (c) Fayed, T. A.; Etaiw, S. E.-D. H.; Landgraf, S.; Grampp, G. Photochem. Photobiol. Sci. 2003, 2, 376.
105. Arient, J. Collect. Czech. Chem. Commun. 1981, 46, 101.
106. Reich, H. J.; Cram, D. J. J. Am. Chem. Soc. 1969, 91, 3527.
107. Renak, M. L.; Bartholomew, G. P.; Wang, S.; Ricatto, P. J.; Lachicotte, R. J.; Bazan, G. C. J. Am. Chem. Soc. 1999, 121, 7787.
108. Pond, S. J. K.; Tsutsumi, O.; Rumi, M.; Kwon, O.; Zojer, E.; Brédas. J.-L.; Marder, S. R.; Perry, J. W. J. Am. Chem. Soc. 2004, 126, 9291.
109. (a) Rumi, M.; Ehrlich, J. E.; Heikai, A. A.; Perry, J. W.; Barlow, S.; Hu, Z.; McCord-Maughon, D.; Parker, T. C.; Röckel, H.; Thayumanavan, S.; Marder, S. R.; Beljonne, D.; Brédas, J.-L. J. Am. Chem. Soc. 2000, 122, 9500.
110. (b) Pond, S. J. K.; Rumi, M.; Levin, M. D.; Parker, T. C.; Beljonne, D.; Day, M. W.; Brédas, J.-L.; Marder, S. R.; Perry, J. W. J. Phys. Chem. A 2002, 106, 11470.
111. Sarker, A. M.; Strehmel, B.; Neckers, D. C. Macromolecules 1999, 32, 7409.
112. Strehmel, B.; Sarker, A. M.; Malpert, J. H.; Strehmel, V.; Seifert, H.; Neckers, D. C. J. Am. Chem. Soc. 1999, 121, 1226.
113. 3), we propose that the dipole of the solvent plays the major role in the solvatochromic shifts. See: (a) Bosque, R.; Sales, J. J. Chem. Inf. Comput. Sci. 2002, 42, 1154.
114. (b) Böttcher, C. J. F. Theory of Electric Polarization; Elsevier Scientific Publishing Co.: Amsterdam, 1973.
115. (a) Castanheira, E. M. S.; Martinho, J. M. G. Chem. Phys. Lett. 1991, 185, 319.
116. (b) Castanheira, E. M. S.; Martinho, J. M. G. J. Photochem. Photobiol. A: Chem. 1994, 80, 151.
117. Suppan, P.; Ghoneim, N. Solvatochromism; The Royal Society of Chemistry: Cambridge, U.K., 1997.
118. Barltrop, J. A.; Coyle, J. D. Principles of Photochemistry; John Wiley and Sons: Chichester, England, 1978.
119. The TS state localized on the [2.2]paracyclophane core contains a degree of π-σπ delocalization via the ethylene bridges; however it arises primarily due to cofacial π-π delocalization. See refs 28c and 29a.
120. The possible participation of solvent polarizability has not been evaluated at this point.
121. (a) Albota, M.; Beljonne, D.; Brédas, J. L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord-Maughon, D.; Perry, J. W.; Röckel, H.; Rumi, M.; Subramaniam, C.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653.
122. (b) de Souza, M. M.; Rumbles, G.; Samuel, I. D. W.; Moratti, S. C.; Holmes, A. B. Synth. Met. 1999, 101, 631.
123. Maciejewski, A.; Steer, R. D. J. Photochem. 1986, 35, 59.
124. Magde, D.; Wong, R.; Seybold, P. G. Photochem. Photobiol. 2002, 75, 327.
125. O'Connor, D. V.; Phillips, D. Time Correlated Single Photon Counting; Academic Press: London, U.K., 1984.