Charge-transfer complexes and energetic disorder in amorphous organic solids

Journal of the American Chemical Society

Volumn 121, Issue 22, 1999, Pages 5340-5341

  Rhodes, Timothy A ^a   Farid, Samir ^a,b   Goodman, Joshua L ^a   Gould, Ian R ^a,b   Young, Ralph H ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

^b EASTMAN KODAK COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL REACTION; CONFORMATION; ELECTRON TRANSPORT; THEORY;

EID: 0033538322     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983586m     Document Type: Article

References (45)

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2. See, for example: (a) James, T. H. In Advances in Photochemistry; Volman, D. H., Hammond, G. S., Gollnick, K., Eds.; John Wiley & Sons: New York, 1986; Vol. 13, p 329. (b) Borsenberger, P. M.; Weiss, D. S. Organic Photoreceptors for Xerography; Marcel Dekker: New York, 1998. (c) Reiser, A. Photoreactive Polymers, the Science and Technology of Resists; Wiley: New York, 1989.
3. See, for example: (a) James, T. H. In Advances in Photochemistry; Volman, D. H., Hammond, G. S., Gollnick, K., Eds.; John Wiley & Sons: New York, 1986; Vol. 13, p 329. (b) Borsenberger, P. M.; Weiss, D. S. Organic Photoreceptors for Xerography; Marcel Dekker: New York, 1998. (c) Reiser, A. Photoreactive Polymers, the Science and Technology of Resists; Wiley: New York, 1989.
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13. For relevant theory, see: (a) Loring, R. F. J. Phys. Chem. 1990, 94, 513. (b) Kador, L. J. Chem. Phys. 1991, 95, 5574. (c) Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Chem. Phys. 1993, 176, 421. For experimental and theoretical work on related systems, see: (d) Fee, R. S.; Milsom, J. A.; Maroncelli, M. J. Phys. Chem. 1991, 95, 5170. (e) Ogrodnik, A.; Keupp, W.; Volk, M.; Aumeier, G.; Michel-Beyerle, M. E. J. Phys. Chem. 1994, 98, 3432. (f) Hartwich, G.; Lossau, H.; Michel-Beyerle, M. E.; Ogrodrnik, A. J. Phys. Chem. 1998, 102, 3815. (g) Murakami, H.; Kushida, T.; Tashiro, H. J. Chem. Phys. 1998, 108, 10309. (h) Bässler, H. Phys. Status Solidi B 1993, 775, 15.
14. For relevant theory, see: (a) Loring, R. F. J. Phys. Chem. 1990, 94, 513. (b) Kador, L. J. Chem. Phys. 1991, 95, 5574. (c) Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Chem. Phys. 1993, 176, 421. For experimental and theoretical work on related systems, see: (d) Fee, R. S.; Milsom, J. A.; Maroncelli, M. J. Phys. Chem. 1991, 95, 5170. (e) Ogrodnik, A.; Keupp, W.; Volk, M.; Aumeier, G.; Michel-Beyerle, M. E. J. Phys. Chem. 1994, 98, 3432. (f) Hartwich, G.; Lossau, H.; Michel-Beyerle, M. E.; Ogrodrnik, A. J. Phys. Chem. 1998, 102, 3815. (g) Murakami, H.; Kushida, T.; Tashiro, H. J. Chem. Phys. 1998, 108, 10309. (h) Bässler, H. Phys. Status Solidi B 1993, 775, 15.
15. For relevant theory, see: (a) Loring, R. F. J. Phys. Chem. 1990, 94, 513. (b) Kador, L. J. Chem. Phys. 1991, 95, 5574. (c) Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Chem. Phys. 1993, 176, 421. For experimental and theoretical work on related systems, see: (d) Fee, R. S.; Milsom, J. A.; Maroncelli, M. J. Phys. Chem. 1991, 95, 5170. (e) Ogrodnik, A.; Keupp, W.; Volk, M.; Aumeier, G.; Michel-Beyerle, M. E. J. Phys. Chem. 1994, 98, 3432. (f) Hartwich, G.; Lossau, H.; Michel-Beyerle, M. E.; Ogrodrnik, A. J. Phys. Chem. 1998, 102, 3815. (g) Murakami, H.; Kushida, T.; Tashiro, H. J. Chem. Phys. 1998, 108, 10309. (h) Bässler, H. Phys. Status Solidi B 1993, 775, 15.
16. For relevant theory, see: (a) Loring, R. F. J. Phys. Chem. 1990, 94, 513. (b) Kador, L. J. Chem. Phys. 1991, 95, 5574. (c) Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Chem. Phys. 1993, 176, 421. For experimental and theoretical work on related systems, see: (d) Fee, R. S.; Milsom, J. A.; Maroncelli, M. J. Phys. Chem. 1991, 95, 5170. (e) Ogrodnik, A.; Keupp, W.; Volk, M.; Aumeier, G.; Michel-Beyerle, M. E. J. Phys. Chem. 1994, 98, 3432. (f) Hartwich, G.; Lossau, H.; Michel-Beyerle, M. E.; Ogrodrnik, A. J. Phys. Chem. 1998, 102, 3815. (g) Murakami, H.; Kushida, T.; Tashiro, H. J. Chem. Phys. 1998, 108, 10309. (h) Bässler, H. Phys. Status Solidi B 1993, 775, 15.
17. For relevant theory, see: (a) Loring, R. F. J. Phys. Chem. 1990, 94, 513. (b) Kador, L. J. Chem. Phys. 1991, 95, 5574. (c) Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Chem. Phys. 1993, 176, 421. For experimental and theoretical work on related systems, see: (d) Fee, R. S.; Milsom, J. A.; Maroncelli, M. J. Phys. Chem. 1991, 95, 5170. (e) Ogrodnik, A.; Keupp, W.; Volk, M.; Aumeier, G.; Michel-Beyerle, M. E. J. Phys. Chem. 1994, 98, 3432. (f) Hartwich, G.; Lossau, H.; Michel-Beyerle, M. E.; Ogrodrnik, A. J. Phys. Chem. 1998, 102, 3815. (g) Murakami, H.; Kushida, T.; Tashiro, H. J. Chem. Phys. 1998, 108, 10309. (h) Bässler, H. Phys. Status Solidi B 1993, 775, 15.
18. For relevant theory, see: (a) Loring, R. F. J. Phys. Chem. 1990, 94, 513. (b) Kador, L. J. Chem. Phys. 1991, 95, 5574. (c) Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Chem. Phys. 1993, 176, 421. For experimental and theoretical work on related systems, see: (d) Fee, R. S.; Milsom, J. A.; Maroncelli, M. J. Phys. Chem. 1991, 95, 5170. (e) Ogrodnik, A.; Keupp, W.; Volk, M.; Aumeier, G.; Michel-Beyerle, M. E. J. Phys. Chem. 1994, 98, 3432. (f) Hartwich, G.; Lossau, H.; Michel-Beyerle, M. E.; Ogrodrnik, A. J. Phys. Chem. 1998, 102, 3815. (g) Murakami, H.; Kushida, T.; Tashiro, H. J. Chem. Phys. 1998, 108, 10309. (h) Bässler, H. Phys. Status Solidi B 1993, 775, 15.
19. For relevant theory, see: (a) Loring, R. F. J. Phys. Chem. 1990, 94, 513. (b) Kador, L. J. Chem. Phys. 1991, 95, 5574. (c) Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Chem. Phys. 1993, 176, 421. For experimental and theoretical work on related systems, see: (d) Fee, R. S.; Milsom, J. A.; Maroncelli, M. J. Phys. Chem. 1991, 95, 5170. (e) Ogrodnik, A.; Keupp, W.; Volk, M.; Aumeier, G.; Michel-Beyerle, M. E. J. Phys. Chem. 1994, 98, 3432. (f) Hartwich, G.; Lossau, H.; Michel-Beyerle, M. E.; Ogrodrnik, A. J. Phys. Chem. 1998, 102, 3815. (g) Murakami, H.; Kushida, T.; Tashiro, H. J. Chem. Phys. 1998, 108, 10309. (h) Bässler, H. Phys. Status Solidi B 1993, 775, 15.
20. (a) Gould, I. R.; Noukakis, D.; Gomez-Jahn, L.; Young, R. H.; Goodman, J. L.; Farid, S. Chem. Phys. 1993, 176, 439.
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26. 4
27. (a) The detailed equations are provided as Supporting Information.
28. 5 In the solid, however, the two processes are competitive.
29. (c) The possibility of energy transfer from a higher-energy excited complex to a lower-energy one can be excluded by concentration experiments. A decrease in the CT complex concentration by more than an order of magnitude did not affect the individual emission and excitation spectra, and the same excitation wavelength dependency was observed as from that at the higher CT concentration.
30. 2 onto 1-in. diameter fused silica windows, which were covered to allow slow evaporation of the solvent. The samples were then purged with nitrogen overnight.
31. For some related studies of CT complexes in rigid media, see: (a) Kobayashi, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 2603. (b) Yokoyama, M.; Endo, Y.; Mikawa, H. Chem. Phys. Lett. 1975, 34, 597. (c) Lachish, U.; Williams, D. J. Chem. Phys. Lett. 1980, 72, 225. (d) Itaya, A.; Egawa, A.; Umehara, Y.; Sakai, H.; Masuhara, H. Polymer 1994, 35, 3149. (e) Miyasaka, H.; Kotani, S.; Itaya, A. J. Phys. Chem. 1995, 99, 5757. (f) Ueda, T.; Fujisawa, R.; Fukumura, H.; Itaya, A.; Masuhara, H. J. Phys. Chem. 1995, 99, 3629. (g) Iwata, S.; Tanaka, J.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 894.
32. For some related studies of CT complexes in rigid media, see: (a) Kobayashi, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 2603. (b) Yokoyama, M.; Endo, Y.; Mikawa, H. Chem. Phys. Lett. 1975, 34, 597. (c) Lachish, U.; Williams, D. J. Chem. Phys. Lett. 1980, 72, 225. (d) Itaya, A.; Egawa, A.; Umehara, Y.; Sakai, H.; Masuhara, H. Polymer 1994, 35, 3149. (e) Miyasaka, H.; Kotani, S.; Itaya, A. J. Phys. Chem. 1995, 99, 5757. (f) Ueda, T.; Fujisawa, R.; Fukumura, H.; Itaya, A.; Masuhara, H. J. Phys. Chem. 1995, 99, 3629. (g) Iwata, S.; Tanaka, J.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 894.
33. For some related studies of CT complexes in rigid media, see: (a) Kobayashi, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 2603. (b) Yokoyama, M.; Endo, Y.; Mikawa, H. Chem. Phys. Lett. 1975, 34, 597. (c) Lachish, U.; Williams, D. J. Chem. Phys. Lett. 1980, 72, 225. (d) Itaya, A.; Egawa, A.; Umehara, Y.; Sakai, H.; Masuhara, H. Polymer 1994, 35, 3149. (e) Miyasaka, H.; Kotani, S.; Itaya, A. J. Phys. Chem. 1995, 99, 5757. (f) Ueda, T.; Fujisawa, R.; Fukumura, H.; Itaya, A.; Masuhara, H. J. Phys. Chem. 1995, 99, 3629. (g) Iwata, S.; Tanaka, J.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 894.
34. For some related studies of CT complexes in rigid media, see: (a) Kobayashi, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 2603. (b) Yokoyama, M.; Endo, Y.; Mikawa, H. Chem. Phys. Lett. 1975, 34, 597. (c) Lachish, U.; Williams, D. J. Chem. Phys. Lett. 1980, 72, 225. (d) Itaya, A.; Egawa, A.; Umehara, Y.; Sakai, H.; Masuhara, H. Polymer 1994, 35, 3149. (e) Miyasaka, H.; Kotani, S.; Itaya, A. J. Phys. Chem. 1995, 99, 5757. (f) Ueda, T.; Fujisawa, R.; Fukumura, H.; Itaya, A.; Masuhara, H. J. Phys. Chem. 1995, 99, 3629. (g) Iwata, S.; Tanaka, J.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 894.
35. For some related studies of CT complexes in rigid media, see: (a) Kobayashi, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 2603. (b) Yokoyama, M.; Endo, Y.; Mikawa, H. Chem. Phys. Lett. 1975, 34, 597. (c) Lachish, U.; Williams, D. J. Chem. Phys. Lett. 1980, 72, 225. (d) Itaya, A.; Egawa, A.; Umehara, Y.; Sakai, H.; Masuhara, H. Polymer 1994, 35, 3149. (e) Miyasaka, H.; Kotani, S.; Itaya, A. J. Phys. Chem. 1995, 99, 5757. (f) Ueda, T.; Fujisawa, R.; Fukumura, H.; Itaya, A.; Masuhara, H. J. Phys. Chem. 1995, 99, 3629. (g) Iwata, S.; Tanaka, J.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 894.
36. For some related studies of CT complexes in rigid media, see: (a) Kobayashi, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 2603. (b) Yokoyama, M.; Endo, Y.; Mikawa, H. Chem. Phys. Lett. 1975, 34, 597. (c) Lachish, U.; Williams, D. J. Chem. Phys. Lett. 1980, 72, 225. (d) Itaya, A.; Egawa, A.; Umehara, Y.; Sakai, H.; Masuhara, H. Polymer 1994, 35, 3149. (e) Miyasaka, H.; Kotani, S.; Itaya, A. J. Phys. Chem. 1995, 99, 5757. (f) Ueda, T.; Fujisawa, R.; Fukumura, H.; Itaya, A.; Masuhara, H. J. Phys. Chem. 1995, 99, 3629. (g) Iwata, S.; Tanaka, J.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 894.
37. For some related studies of CT complexes in rigid media, see: (a) Kobayashi, T.; Yoshihara, K.; Nagakura, S. Bull. Chem. Soc. Jpn. 1971, 44, 2603. (b) Yokoyama, M.; Endo, Y.; Mikawa, H. Chem. Phys. Lett. 1975, 34, 597. (c) Lachish, U.; Williams, D. J. Chem. Phys. Lett. 1980, 72, 225. (d) Itaya, A.; Egawa, A.; Umehara, Y.; Sakai, H.; Masuhara, H. Polymer 1994, 35, 3149. (e) Miyasaka, H.; Kotani, S.; Itaya, A. J. Phys. Chem. 1995, 99, 5757. (f) Ueda, T.; Fujisawa, R.; Fukumura, H.; Itaya, A.; Masuhara, H. J. Phys. Chem. 1995, 99, 3629. (g) Iwata, S.; Tanaka, J.; Nagakura, S. J. Am. Chem. Soc. 1966, 88, 894.
38. For emission spectra in photons/sec/nm, the maximum of the emission spectrum varies from 537 to 554 nm as the excitation wavelength is varied from 430 to 470 nm.
39. 5a,12c No fast relaxation comparable to that observed in solution is observed in time-resolved emission experiments in the polymer, from which we conclude that the relaxation does not occur in this case.
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44. 14a
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