Energy- and hole-transfer dynamics in oxidized porphyrin dyads

Journal of Physical Chemistry B

Volumn 113, Issue 1, 2009, Pages 54-63

  Song, Hee Eun ^a   Kirmaier, Christine ^a   Diers, James R ^c   Lindsey, Jonathan S ^b   Bocian, David F ^c   Holten, Dewey ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; DYNAMICS; ELECTROCHEMICAL OXIDATION; EXCITED STATES; GROUND STATE; NITROGEN COMPOUNDS; QUENCHING; RATE CONSTANTS; ZINC; ZINC COMPOUNDS;

ARYL RINGS; CONNECTION SITES; DIPHENYLETHYNE; ELECTRON DENSITIES; ELECTRONIC COUPLINGS; EXCITED-STATE ENERGIES; FREE BASE; FREE BASE PORPHYRINS; HOLE TRANSFERS; MULTIPORPHYRIN; ORBITAL OVERLAPS; TIME-RESOLVED ABSORPTIONS; TRANSFER PATHWAYS; TWO CHANNELS; ZINC PORPHYRINS;

PORPHYRINS;

EID: 61949343225     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp8060637     Document Type: Article

References (73)

1. Nakamura, Y.; Aratani, N.; Osuka, A. Chem. Soc. Rev. 2007, 36, 831-845.
2. Imahori, H. J. Phys. Chem. B 2004, 108, 6130-6143.
3. Imahori, H. Org. Biomol. Chem. 2004, 2, 1425-1433.
4. Harvey, P. D. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2003; Vol. 18, pp 63-250.
5. Kim, D.; Osuka, A. J. Phys. Chem. A 2003, 107, 8791-8816.
6. Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57-69.
7. Aratani, N.; Osuka, A. Macromol. Rapid Commun. 2001, 22, 725-740.
8. Burrell, A. K.; Officer, D. L.; Plieger, P. G.; Reid, D. C. W. Chem. Rev. 2001, 101, 2751-2796.
9. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40-48.
10. Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 153-190.
11. Kurreck, H.; Huber, M. Angew. Chem. Int. Ed. Engl. 1995, 34, 849-866.
12. Gribkova, S. E.; Evstigneeva, R. P.; Luzgina, V. N. Russ. Chem. Rev. 1993, 62, 963-979.
13. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205.
14. Wasielewski, M. R. Chem. Rev. 1992, 92, 435-461.
15. Wasielewski, M. R. In Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, FL, 1991; pp 269-286.
16. Gust, D.; Moore, T. A. Top. Curr. Chem. 1991, 159, 103-151.
17. Borovkov, V. V.; Evstigneeva, R. P.; Strekova, L. N.; Filippovich, E. I. Russ. Chem. Rev. 1989, 58, 602-619.
18. Gust, D.; Moore, T. A. Science 1989, 244, 35-41.
19. Boxer, S. G. Biochim. Biophys. Acta 1983, 726, 265-292.
20. Krause, G. H.; Weis, E. Ann. Rev. Plant Physiol. Plant Mol. Biol. 1991, 42, 313-349.
21. Ahn, T. K.; Avenson, T. J.; Ballottari, M.; Cheng, Y.-C.; Niyogi, K. K.; Bassi, R.; Fleming, G. R. Science 2008, 320, 794-797.
22. Wagner, R. W.; Lindsey, J. S.; Seth, J.; Palaniappan, V.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 3996-3997.
23. Ambroise, A.; Wagner, R. W.; Rao, P. D.; Riggs, J. A.; Hascoat, P.; Diers, J. R.; Seth, J.; Lammi, R. K.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Chem. Mater. 2001, 13, 1023-1034.
24. Lammi, R. K.; Wagner, R. W.; Ambroise, A.; Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Phys. Chem. B 2001, 105, 5341-5352.
25. Banin, U.; Bruchez, M.; Alivisatos, A. P.; Ha, T.; Weiss, S.; Chemla, D. S. J. Chem. Phys. 1999, 110, 1195-1201.
26. Shimizu, K. T.; Neuhauser, R. G.; Leatherdale, C. A.; Empedocles, S. A.; Woo, W. K.; Bawendi, M. G. Phys. Rev. B 2001, 63, 205316.
27. Verberk, R.; van Oijen, A. M.; Orrit, M. Phys. Rev. B 2002, 66, 233202.
28. Zhang, K.; Chang, H.; Fu, A.; Alivisatos, A. P.; Yang, H. Nano Lett. 2006, 6, 843-847.
29. Gesquiere, A. J.; Park, S.-J.; Barbara, P. F. J. Am. Chem. Soc. 2005, 127, 9556-9560.
30. Barbara, P. F.; Gesquiere, A. J.; Park, S.-J.; Lee, Y. J. Acc. Chem. Res. 2005, 38, 602-610.
31. Palacios, R. E.; Fan, F.-R. F.; Grey, J. K.; Suk, J.; Bard, A. J.; Barbara, P. F. Nat. Mater. 2007, 6, 680-685.
32. Lammi, R. K.; Ambroise, A.; Wagner, R. W.; Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey, J. S Chem. Phys. Lett. 2001, 341, 35-44.
33. +* refers to the free base porphyrin in the ground state, excited state, ground state π-cation radical, or excited-state π-cation radical, respectively.
34. Hsiao, J.-S.; Krueger, B. P.; Wagner, R. W.; Johnson, T. E.; 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.
35. Yang, S. I.; Seth, J.; Balasubramanian, T.; Kim, D.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Am. Chem. Soc. 1999, 121, 4008-4018.
36. The term "hole transfer" is used herein even though the net transport of a hole could occur via either direct hole migration or electron migration in the reverse direction.
37. Wagner, R. W.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1996, 118, 11166-11180.
38. Balasubramanian, T.; Lindsey, J. S. Tetrahedron 1999, 55, 6117-6784.
39. Seth, J.; Palaniappan, V.; Wagner, R. W.; Johnson, T. E.; Lindsey, J. S.; Bocian, D. F. J. Am. Chem. Soc. 1996, 118, 11194-11207.
40. Yang, S. I.; Seth, J.; Strachan, J.-P.; Gentemann, S.; Kim, D.; Holten, D.; Lindsey, J. S.; Bocian, D. F. J. Porphyrins Phthalocyanines 1999, 3, 117-147.
41. Seybold, P. G.; Gouterman, M. J. Mol. Spectrosc. 1969, 31, 1-13.
42. 41
43. (b) Gradyushko, A. T.; Sevchenko, A. N.; Solovyov, K. N.; Tsvirko, M. P. Photochem. Photobiol. 1970, 11, 387-400.
44. Kee, H. L.; Kirmaier, C.; Yu, L.; Thamyongkit, P.; Youngblood, W. J.; Calder, M. E.; Ramos, L.; Noll, B. C.; Bocian, D. F.; Scheidt, W. R.; Birge, R. R.; Lindsey, J. S.; Holten, D. J. Phys. Chem. B 2005, 109, 20433-20443.
45. Yang, S. I.; Lammi, R. K.; Prathapan, S.; Miller, M. A.; Seth, J.; Diers, J. R.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Mater. Chem. 2001, 11, 2420-2430.
46. del Rosario Benites, M.; Johnson, T. E.; Weghorn, S.; Yu, L.; Rao, P. D.; Diers, J. R.; Yang, S. I.; Kirmaier, C.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Mater. Chem. 2002, 12, 65-80.
47. Hindin, E.; Forties, R. A.; Loewe, R. S.; Ambroise, A.; Kirmaier, C.; Bocian, D. F.; Lindsey, J. S.; Holten, D.; Knox, R. S. J. Phys. Chem. B 2004, 108, 12821-12832.
48. Dixon, J. M.; Taniguchi, M.; Lindsey, J. S. Photochem. Photobiol. 2005, 81, 212-213.
49. Barshop, B. A.; Wrenn, R. F.; Frieden, C. Anal. Biochem. 1983, 130, 134-145.
50. Song, H.-E.; Kirmaier, C.; Schwartz, J. K.; Hindin, E.; Yu, L.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Phys. Chem. B 2006, 110, 19121-19130.
51. Song, H.-E.; Kirmaier, C.; Schwartz, J. K.; Hindin, E.; Yu, L.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Phys. Chem. B 2006, 110, 19131-19139.
52. Li, F.; Gentemann, S.; Kalsbeck, W. A.; Seth, J.; Lindsey, J. S.; Holten, D.; Bocian, D. F. J. Mater. Chem. 1997, 7, 1245-1262.
53. Tomizaki, K.-Y.; Loewe, R. S.; Kirmaier, C.; Schwartz, J. K.; Retsek, J. L.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Org. Chem. 2002, 67, 6519-6534.
54. Thamyongkit, P.; Muresan, A. Z.; Diers, J. R.; Holten, D.; Bocian, D. F.; Lindsey, J. S. J. Org. Chem. 2007, 72, 5207-5217.
55. Felton, R. H. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 5, pp 53-125.
56. Rodriguez, J.; Holten, D. J. Chem. Phys. 1989, 91, 3525-3531.
57. Rodriguez, J.; Kirmaier, C.; Holten, D. J. Chem. Phys. 1991, 94, 6020-6029.
58. Bilsel, O.; Milam, S. N.; Girolami, G. S.; Suslick, K. S.; Holten, D. J. Phys. Chem. 1993, 97, 7216-7221.
59. Barley, M.; Dolphin, D.; James, B. R.; Kirmaier, C.; Holten, D. J. Am. Chem. Soc. 1984, 106, 3937-3943.
60. Lee, M.; Song, O.-K.; Seo, J.-C.; Kim, D.; Kim, H.-J.; Kim, K. J. Phys. Chem. 1992, 96, 8374-8377.
61. Fajer, J.; Borg, D. C.; Forman, A.; Dolphin, D.; Felton, R. H. J. Am. Chem. Soc. 1970, 92, 3451-3459.
62. Osuka, A.; Zhang, R.-P.; Maruyama, K.; Mataga, N.; Tanaka, Y.; Okada, T. Chem. Phys. Lett. 1993, 215, 179-184.
63. In global-analysis amplitude spectra, a time-evolving kinetic component will have negative amplitude at wavelengths that correspond to either growth of a transient absorption or decay of a bleaching (i.e., ΔA changes in a positive direction with increasing time) and positive amplitude at wavelengths corresponding to either decay of a transient absorption or growth of a bleaching (i.e., ΔA changes in a negative direction with increasing time).
64. Rodriguez, J.; Kirmaier, C.; Holten, D. J. Am. Chem. Soc. 1989, 111, 6500-6506.
65. Kilsa, K.; Kajanus, J.; Mårtensson, J.; Albinsson, B. J. Phys. Chem. B 1999, 103, 7329-7339.
66. Cho, H. S.; Jeong, D. H.; Yoon, M.-C.; Kim, Y. H.; Kim, Y.-R.; Kim, D.; Jeoung, S. C.; Kim, S. K.; Aratani, N.; Shinmori, H.; Osuka, A. J. Phys. Chem. A 2001, 105, 4200-4210.
67. Okuno, Y.; Mashiko, S. Jpn. J. Appl. Phys. 2006, 45, 475-478.
68. Okuno, Y.; Mashiko, S Thin Solid Films 2003, 438-439, 215-220.
69. Gouterman, M. In The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. 3, pp 1-165.
70. Sibilia, S. A.; Czernuszewicz, R. S.; Crossley, M. J.; Spiro, T. G. Inorg. Chem. 1997, 36, 6450-6453.
71. Petit, L.; Quartarolo, A.; Adamo, C.; Russo, N. J. Phys. Chem. B 2006, 110, 2398-2404.
72. Song, H.-E.; Kirmaier, C.; Taniguchi, M.; Diers, J. R.; Bocian, D. F.; Lindsey, J. S.; Holten, D. J. Am. Chem. Soc. 2008, 130, 15636-15648.
73. Song, H.-E.; Kirmaier, C.; Taniguchi, M.; Bocian, D. F.; Lindsey, J. S.; Holten, D. Photochem. Photobiol., in press.