Effects of orbital ordering on electronic communication in multiporphyrin arrays

Journal of the American Chemical Society

Volumn 119, Issue 46, 1997, Pages 11191-11201

  Strachan, Jon Paul ^a   Gentemann, Steve ^b   Seth, Jyoti ^c   Kalsbeck, William A ^c   Lindsey, Jonathan S ^a   Holten, Dewey ^b   Bocian, David F ^c  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b WASHINGTON UNIVERSITY   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ARRAYS; CARRIER CONCENTRATION; CHARGE TRANSFER; DESIGN; ELECTRON ENERGY LEVELS; ENERGY TRANSFER; MOLECULAR ORIENTATION; ORGANIC COMPOUNDS; SPECTROSCOPY; ZINC COMPOUNDS;

MULTIPORPHYRIN ARRAYS; ORBITAL ORDERING;

OPTOELECTRONIC DEVICES;

PORPHYRIN DERIVATIVE;

ARTICLE; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; ENERGY TRANSFER; FLUORESCENCE; MOLECULAR DYNAMICS; PHOTOCHEMISTRY; RAMAN SPECTROMETRY; SPECTROPHOTOMETRY; THERMODYNAMICS;

EID: 1842415454     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971678q     Document Type: Article

References (68)

1. (a) McDermott, G.; Prince, S. M.; Freer, A. A.; Hawethornthwaite-Lawless, A. M.; Papiz, M. Z.; Cogdell, R. J.; Isaacs, N. W. Nature 1995, 374, 517-521.
2. (b) Karrasch, S.; Bullough, P. A.; Ghosh, R. EMBO J. 1995, 14, 631-638.
3. (c) Deisenhofer, J.; Norris, J. R., Eds. The Photosynthetic Reaction Center; Academic: San Diego, CA 1993; Vol. II.
4. (d) Breton, J.; Verméglio, A., Eds. NATO Ser. A 1992, 237.
5. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
6. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
7. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
8. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
9. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
10. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
11. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
12. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
13. For reviews, see: (a) Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292. (b) Gust, D.; Moore, T. A. Science 1989, 244, 35-41. (c) Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619. (d) Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151. (e) Wasielewski, M. R. In Chhrophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286. (f) Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461. (g) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205. (h) Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979. (i) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
14. Prathapan, S.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1993, 115, 7519-7520.
15. Wagner, R. W.; Lindsey, J. S. J. Am. Chem. Soc. 1994, 116, 9759-9760.
16. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996-3997.
17. Bothner-By, A. A.; Dadok, J.; Johnson, T. E.; Lindsey, J. S. J. Phys. Chem. 1996, 100, 17551-17557.
18. Seth, J.; Palaniappan, V.; Johnson, T. E.; Prathapan, S.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1994, 116, 10578-10592.
19. Hsiao, J.-S.; Krueger, B. P.; Wagner, R. W.; Delaney, J. K.; Mauzerall, D. C.; Fleming, G. R.; Lindsey, J. S.; Bocian, D. F.; Donohoe, R. J. J. Am. Chem. Soc. 1996, 118, 11181-11193.
20. Seth, J.; Palaniappan, V.; Wagner, R. W.; Johnson, T. E.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 11194-11207.
21. Li, F.; Gentemann, S.; Kalsbeck, W. A.; Seth, J.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Mater. Chem. 1997, 7, 1245-1262.
22. Wagner, R. W.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1996, 118, 11166-11180.
23. -1, which is used throughout this paper.
24. Osuka, A.; Tanabe, N.; Kawabata, S.; Yamazaki, I.; Nishimura, Y. J. Org. Chem. 1995, 60, 7177-7185.
25. -1.
26. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. III, pp 1-165.
27. Fujii, H. Chem. Lett. 1994, 1491-1494.
28. Spellane, J. P.; Gouterman, M.; Antipas, A.; Kim, S.; Liu, Y. C. Inorg. Chem. 1980, 19, 386-391.
29. Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1989, 54, 828-836.
30. Austin, W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280-2286.
31. Lindsey, J. S.; Prathapan, S.; Johnson, T. E.; Wagner, K. W. Tetrahedron 1994, 50, 8941-8968.
32. Wagner, R. W.; Johnson, T. E.; Li, F.; Lindsey, J. S. J. Org. Chem. 1995, 60, 5266-5273.
33. Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1-13.
34. 30ZnFbU (Table 1).
35. Rodriguez, J.; Kirmaier, C.; Holten, D. J. Am. Chem. Soc. 1989, 111, 6500-6506.
36. (a) Felton, R. H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. V, pp 53-126.
37. (b) Davis, D. G. In The Porphvrins; Dolphin, D., Ed.; Academic Press: New York, 1978, Vol. V, pp 127-152.
38. Collman, J. P.; Hampton, P. D.; Brauman, J. I. J. Am. Chem. Soc. 1990, 112, 2986-2998.
39. (a) Barzilay, C.; Sibilia, S. A.; Spiro, T. G.; Gross, Z. Chem.-Eur. J. 1995, 1, 222-231.
40. (b) Gross, Z.; Barzilay, C. Angew. Chem., Int. Ed. Engl. 1992, 31, 1615-1617.
41. Ghosh, A. J. Am. Chem. Soc. 1995, 117, 4691-4699.
42. Cariou, M.; Simonet, J. J. Chem. Soc., Chem. Commun. 1990, 445-446.
43. Armitage, J. B.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1954, 147-154.
44. Heath, G. A.; Yellowlees, L. J.; Braterman, P. S. J. Chem. Soc., Chem. Commun. 1981, 287-289.
45. Elliot, C. M.; Hershenhart, E. J. Am. Chem. Soc. 1982, 104, 7519-7526.
46. Edwards, W. D.; Zerner, M. C. Can. J. Chem. 1985, 63, 1763-1772.
47. (a) Angel, S. M.; DeArmond, M. K.; Donohoe, R. J.; Wertz, D. W. J. Phys. Chem. 1985, 89, 282-285.
48. (b) Donohoe, R. J.; Tait, C. D.; DeArmond, M. K.; Wertz, D. W. Spectrochim. Acta 1986, 42A, 233-240.
49. (c) Tait, C. D.; MacQueen, D. B.; Donohoe, R. J.; DeArmond, M. K.; Hanck, K. W.; Wertz, D. W. J. Phys. Chem. 1986, 90, 1766-1771.
50. (d) Donohoe, R. R.; Tait, C. D.; DeArmond, M. K.; Wertz, D. W. J. Phys. Chem. 1986, 90, 3923-3926.
51. (e) Donohoe, R. J.; Tait, C. D.; DeArmond, M. K.; Wertz, D. W. J. Phys. Chem. 1986, 90, 3927-3930.
52. Fajer, J.; Davis, M. S. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York. 1979; Vol. IV, pp 197-256.
53. (a) Wertz, J. E.; Bolton, J. R. Electron Spin Resonance: Elementary Theory and Practical Applications; McGraw-Hill: New York, 1972; pp 223-257.
54. (b) Carrington, A.; McLachlan, A. D. Introduction to Magnetic Resonance; Harper and Row: New York, 1967; pp 115-131.
55. Lamola, A. A. In Energy Transfer and Organic Photochemistry; Lamola, A. A., Turro, N. J., Eds.; Interscience: New York, 1969.
56. (a) Anton, J. A.; Loach, P. A.; Govindjee Pholochem. Photobiol. 1978, 28, 235-242.
57. (b) Brookfield, R. L.; Ellul, H.; Harriman, A.; Porter, G. J. Chem. Soc., Faraday Trans. 2 1986, 82, 219-233.
58. (c) Osuka, A.; Maruyama, K.; Yamazaki, I.; Tamai, N. Chem. Phys. Lett. 1990, 165, 392-396.
59. (d) Gust, D.; Moore, T. A.; Moore, A. L.; Gao, F.; Luttrull, D.; DeGraziano, J. M.; Ma, X. C.; Makings, L. R.; Lee, S-J.; Trier, T. T.; Bittersmann, E.; Seely, G. R.; Woodward, S.; Bensasson, R. V.; Rougée, M.; De Schryver, F. C.; Van der Auweraer, M. J. Am. Chem. Soc. 1991, 113, 3638-3649.
60. (e) Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995, 117, 704-714.
61. 15
62. Kuciauskas, D.; Liddell, P. A.; Hung, S. C.; Lin, S.; Stone, S.; Seely, G. R.; Moore, A. L.; Moore, T. A.; Gust, D. J. Phys. Chem. B 1997, 101, 429-440.
63. Weiss, C. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1979; Vol. III, pp 211-223.
64. (a) Osuka, A.; Marumo, S.; Maruyama, K.; Mataga, N.; Tanaka, Y.; Taniguchi, S.; Okada, T.; Yamazaki, I.; Nishimura, Y. Bull. Chem. Soc. Jpn. 1995, 68, 262-276.
65. (b) Osuka, A.; Marumo, S.; Wada, Y.; Yamazaki, I.; Yamazaki, T.; Shirakawa, Y.; Nishimura, Y. Bull. Chem. Soc. Jpn. 1995, 68, 2909-2915.
66. (c) Osuka, A.; Marumo, S.; Mataga, N.; Taniguchi, S.; Okada, T.; Yamazaki, Y.; Nishimura, Y.; Ohno, T.; Nozaki, K. J. Am. Chem. Soc. 1996, 118, 155-168.
67. (d) Osuka, A.; Wada, Y.; Maruyama, K.; Tamiaki, H. Heterocycles 1997, 44, 165-168.
68. (e) Zheng, G.; Pandey, R. K.; Forsyth, T. P.; Kozyrev, A. N.; Dougherty, T. J.; Smith, K. M. Tetrahedron Lett. 1997, 38, 2409-2412.