Reorganization energies of diprotonated and saddle-distorted porphyrins in photoinduced electron-transfer reduction controlled by conformational distortion

Journal of the American Chemical Society

Volumn 131, Issue 2, 2009, Pages 577-584

  Nakanishi, Tatsuaki ^a   Ohkubo, Kei ^a   Kojima, Takahiko ^a   Fukuzumi, Shunichi ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON DONORS; ELECTRON TRANSFER; HYDROCHLORIDE SALTS; LASER FLASH PHOTOLYSIS; LINEAR CORRELATION; MARCUS THEORY; OUT-OF-PLANE DISPLACEMENT; PENTAFLUOROPHENYL; PHOTO-INDUCED ELECTRON TRANSFER; PORPHYRIN RINGS; REORGANIZATION ENERGIES; SOLVENT REORGANIZATION ENERGY; STRUCTURAL CHANGE; TETRAKIS; TETRAPHENYL PORPHYRINS;

ACETONITRILE; ELECTRON TRANSITIONS; PHOTOLYSIS; THERMOMECHANICAL PULPING PROCESS; ZINC; ZINC COMPOUNDS;

PORPHYRINS;

ACETONITRILE; CHLORIDE; DODECAPHENYLPORPHYRIN; OCTAPHENYLPORPHYRIN; PORPHYRIN; PORPHYRIN DERIVATIVE; TETRAKIS(2,4,6 TRIMETHYLPHENYL)PORPHYRIN; TETRAPHENYLPORPHYRIN; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CORRELATION ANALYSIS; ELECTRON TRANSPORT; ENERGY; KINETICS; LIGHT; PHOTOLYSIS;

EID: 67749103840     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja806261q     Document Type: Article

References (82)

1. Fukuzumi, S. In The Porphyrin Handbook; Kadish. K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego. CA; 2000; Vol. 8, p 115.
2. (a) Deisenhofer, J.; Michel, H. Angew. Chem., Int. Ed. Engl. 1989, 28, 829.
3. (b) von Jagow, G.; Engel, W. D. Angew. Chem. Int. Ed. Engl. 1980, 19, 659.
4. Dickerson, R. E.; Timkovich, R. The Enzymes, 3rd ed.: Boyer, P., Ed.; Academic Press: New York, 1975; Vol. 11, p 397.
5. Kaim, W.; Schwederski, B. Bioinorganic Chemistry: Inorganic Elements in the Chemistty of Life; Wiley: New York, 1994.
6. Margoliash, E. In Electron Transport and Oxygen Utilization; Ho, C., Ed.; Elsevier: New York, 1982.
7. Isied, S. S. Prog. Inorg. Chem. 1984, 32, 443.
8. Meyer, T. E.; Kamen, M. D. Adv. Protein Chem. 1982, 35, 105.
9. Sigel, H.; Sigel, A., Eds. Electron Transfer Reactions in Metalloproleins, in Metal Ions in Biological Systems; Marcel Dekker: New York, 1991; Vol. 27.
10. Moore, G. R.; Pettigrew, G. W. Cytochromes c: Springer-Verlag: Berlin, 1990.
11. Fukuzumi, S.; Imahori, H. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2, p 927.
12. Kadish, K. M.; Van-Caemelbecke, E.; Royal, G. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 2000; Vol. 8, p 1.
13. Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard. R., Eds.; Academic Press: New York, 2000; Vol. 8, p 153.
14. (a) Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155.
15. (b) Marcus, R. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1111.
16. For X values for metal-eentered electron-transfer reactions of metalloporphyrins, see:(a) Fukuzumi, S.; Nakanishi, I.; Tanaka, K.; Suenobu, T.; Tabard, A.; Guilard, R.; Van Caemelbecke. E.; Kadish, K. M. J. Am. Chem. Soc. 1999, 121, 785.
17. (a) Horning, T. L.; Fujita, E.; Fajer, J. J. Am. Chem. Soc. 1986, 108, 323.
18. (b) Barkigia, K. M.; Renner, M. W.; Genge, M. O.; Fajer, J. J. J. Phys. Chem. B 2004, 108, 2173.
19. (c) Marcelli, A.; Foggi, P.; Moroni, L.; Gellini. C.; Salvi, P. R.; Badovinac, I. J. J. Phys. Chem. A 2007, 111, 2276.
20. (d) Marcelli, A.; Foggi, P.; Moroni, L.; Gellini, C.; Salvi, P. R. J. Phys. Chem. A 2008, 112, 1864.
21. (a) Gentemann, S.; Medfoith, C. J.; Forsyth, T. P.; Nurco, D. J.; Smith, K. M.; Fajer, J.; Holten, D. J. Am. Chem. Soc. 1994, 116, 7363.
22. (b) Caignan, G. A.; Deshmukh, R.; Zeng, Y.; Wilks. A.; Buncec, R. A.; Rivera, M. J. Am. Chem. Soc. 2003, 125, 11842.
23. (c) Sigfridsson, E.; Ryde, U. J. Biol. Inorg. Chem. 2003, 8, 272.
24. (d) Shi, Z.; Franco, R.; Haddad. R.; Shelnutt. J. A.; Ferreira. G. C. Biochemistry 2006, 45. 2904.
25. (a) Alden, R. G.; Ondrias, M. R.; Shelnutt, J. A. J. Am. Chem. Soc. 1990, 112, 691.
26. (b) Cowley, A. B.; Lukat-Rodgers, G. S.; Rodgers, K. R.; Benson, D. R. Biochemistry 2004, 43, 1656.
27. (c) Cowley, A. B.; Benson, D. R. Inorg. Chem. 2007, 46, 48.
28. (d) Mbofana, C.; Zimmer, M. Inorg. Chem. 2006, 45, 2598.
29. (a) Barkigia, K. M.; Chantranupong. L.; Smith. K. M.; Fajer, J. J. Am. Chem. Soc. 1988. 110, 7566.
30. (b) Michel, L. V.; Ye, T.; Bowman, S. E. J.; Levin, B. D.; Hahn, M. A.; Russell, B. S.; Elliott, S. J.; Bren, K. L. Biochemistry 2007, 46, 11753.
31. (a) Shelnutt, J. A.; Medfoith, C. J.; Berber, M. D.; Barkigia, K. M.; Smith, K. M. J. Am. Chem. Soc. 1991, 113, 4077.
32. (b) Medforth, C. J.; Senge, M. O.; Smith, K. M.; Sparks, L. D.; Shelnutt, J. A. J. Am. Chem. Soc. 1992, 114, 9859.
33. (c) Nurco, D. J.; Medforth, C. J.; Forsyth, T. P.; Olmstead, M. M.; Smith, K. M. J. Am. Chem. Soc. 1996, 118, 10918.
34. (d) Nurco, D. J.; Barkigia, K. M.; Renner, M. W.; Melamed, D.; Smith, K.; Fajer, J. Phys. Chem. B 1998, 102, 322.
35. Takeda, J.; Ohya, T.; Sato, M. Inorg. Chem. 1992, 31, 2877.
36. Medforth, C. J.; Hobbs, J. D.; Rodriguez, M. R.; Abraham, R. J.; Smith, K. M.; Shelnutt, J. A. Inorg. Chem. 1995, 34, 1333.
37. Shelnutt, J. A.; Majumder, S. A.; Sparks, L. D.; Hobbs, J. D.; Medforth, C. J.; Senge, M. O.; Smith, K. M.; Miura, M.; Luo, L.; Quirke, J. M. E. J. Raman Spectrosc. 1992, 23, 523.
38. (a) Medforth, C. J.; Smith, K. M. Tetrahedron Lett. 1990, 31, 5583.
39. (b) Gentemann, S.; Medforth, C. J.; Forsyth, T. P.; Nurco, D. J.; Smith, K. M.; Fajer, J.; Holten. D J. Am. Chem. Soc. 1994, 116, 7363.
40. (c) Drain, C. M.; Kirmaier, C.; Medforth, C. J.; Nurco, D. J.; Smith, K. M.; Holten, D. Phys. Chem. 1996, 100, 11984.
41. (d) Gentemann, S.; Nelson, N. Y.; Jaquinod, L.; Nulco, D. J.; Leung, S. H.; Medforth, C. J.; Smith, K. M.: Fajer, J.; Holten, D. Phys. Chem. B 1997, 101. 1247.
42. (e) Retsek, J. L.; Gentemann, S.; Medforth, C. J.; Smith, K. M.; Chirvony, V. S.; Fafer, J.; Holten, D. Phys. Chem. B 2000, 104, 6690.
43. (f) Savenkova, N. S.; Kuznetsova, R. T.; Lapin, I. N.; Svetlichnyi, V. A.; Mayer. G. V.; Shatunov. P. A. Opt. Spectrosc. 2005, 99, 751.
44. (a) Harada, R.; Kojima, T. Chem. Commun. 2005, 716.
45. (b) Kojima, T.; Nakanishi, T.; Harada, R.; Ohkubo, K.; Yamauchi, S.; Fukuzumi, S. Chem.-Eur. J. 2007, 11, 8714.
46. (c) Fukuzumi, S.; Kojima, T. J. Mater. Chem. 2008, 18, 1427.
47. Utilization of H2DPP as a ligand to the Mo(V) center has allowed us to access a "porphyrin nanotube" including unstable and unprecedented tetranuclear Mo(VI) - oxo clusters in its inner space, see:Harada, R.; Matsuda. Y.; Okawa, H.; Kojima, T. Angew. Chem., Int. Ed. 2004, 43, 1825.
48. Both protonation of the porphyrin and the substituent groups of the porphyrin play an important role in attaining the ordered assemblies with single-walled carbon nanotubes, see:(a) Hasobe, T.; Fukuzumi, S.; Kamat, P. V. J. Am. Chem. Soc. 2005. 127, 11884.
49. (b) Hasobe, T.; Fukuzumi, S.; Kamat, P. V. Phys. Chem. B 2006, 110, 25477.
50. For electron donor-acceptor dyads in which porphyrins are used as electron acceptors, see:(a) Kashiwagi, Y.; Imahori. H.; Araki, Y.; Ito, O.; Yamada, K.; Sakata, Y.; Fukuzumi, S. Phys. Chem. A 2003, 107, 5515.
51. (b) Kubo, M.; Mori, Y.; Otani, M.; Murakami, M.; Ishibashi, Y.; Yasuda, M.; Hosomizu, K.; Miyasaka, H.; Imahori, H.; Nakashima, S. Phys. Chem. A 2007, 111, 5136.
52. Fukuzumi, S.; Nakanishi, I.; Barbe, J.-M.; Guilard, R.; Van Caemelbecke, E.; Guo, N.; Kadish, K. M. Angew. Chem., Int. Ed. 1999. 38, 964.
53. (a) Kadish, K. M.; E, W.; Ou, Z.; Shao, J.; Sintic, P. J.; Ohkubo, K.; Fukuzumi, S.; Crossley, M. J. Chem. Commun. 2002, 356.
54. (b) Ou, Z.; Kadish, K. M.; E. W.: Shao, J.; Sintic, P. J.; Ohkubo. K.; Fukuzumi, S.; Crossley, M. J. Inorg. Chem. 2004, 43, 2078.
55. Fukuzumi, S.; Ohkubo, K.; E, W.; Ou, Z.; Shao, J.; Kadish, K. M.; Hutchison, J. A.; Ghiggino, K. P.; Sintic, P. J.; Crossley, M. J. J. Am. Chem. Soc. 2003, 125, 14984.
56. (a) Chan, K. S.; Zhou, X.; Luo, B.-S.; Mak, T. C. W. J. Chem. Soc., Chem. Commun. 1995, 733.
57. (b) Liu, C-J.; Yu, W.-Y.; Peng, S.-M.; Mak, T. C. W.; Che, C-M. J. Chem. Soc, Dalton Trans. 1998, 1805.
58. Adler, A. D.; Longo, F. R.; Finarell, J.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32.
59. The SHACV method provides a superior approach to directly evaluate the one-electron redox potentials in the presence of a follow-up chemical reaction relative to the better-known dc and fundamental harmonic ac methods:(a) Bond. A. M.; Smith. D. E. Anal. Chem. 1974, 46, 1946.
60. (b) Arnett, E. M.; Amarnath, K.; Harvey, N. G.; Cheng, J.-P. J. Am. Chem. Soc. 1990, 112, 344.
61. Bard, A. J.; Faulkner, L. R. Electrochemical Methods, Fundamental and Applications; John Wiley & Sons: New York. 2001; Chapter 10, pp 368-416.
62. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Non-aqueous Systems; Mercel Dekker: New York, 1970.
63. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
64. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
65. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. The full list of authors is given in the Supporting Information.
66. Dennington, R., II; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. Semichem, Inc.: Shawnee Mission, KS, 2003.
67. Grampp, G.; Neubauer, K. J. Chem. Soc., Perkin Trans. 2 1993, 2015.
68. (a) Avdievich, N. I.; Jeevarajan, A. S.; Forbes, M. D. E. J. Phys. Chem. 1996, 100. 5334.
69. (b) Yamauchi, J.; Fujita. H. Bull. Chem. Soc. Jpn. 1990, 63, 2928.
70. (a) Rehm, D.; Weller, A. Ber. Bunsen-ges Phys. Chem. 1969, 73, 834.
71. (b) Rehm, D.; Weller, A. Isr, J. Chem. 1970, 8, 259.
72. Kavarnos, G. J. Fundamentals of Photoinduced Electron Transfer; Wiley-VCH: New York, 1993.
73. Brunschwig, B. S.; Ehrenson. S.; Sutin, N. J. J. Am. Chem. Soc. 1984, 106, 6858.
74. Crystal structures of tetraphenylporphyrin diacids:(a) Stone, A.; Fleischer, B. J. Am. Chem. Soc 1968, 90, 2735.
75. (b) Fleischer, E. B. Acc. Chem. Res. 1970, 3, 105.
76. (c) Cheng, B.; Munro. O. Q.; Marques, H. M.; Scheidt, W. R. J. Am. Chem. Soc. 1997, 119, 10732.
77. (d) Juillard, S.; Ferrand, Y.; Simonneaux, G.; Toupet, L. Tetrahedron 2005, 61, 3489.
78. (e) Ravati. S.: Zakavi, S.; Ghaemi, A.: Carroll, P. J. Tetrahedron Lett. 2008, 49, 664.
79. Birnbaum, E. R.; Hodge, J. A.; Grinstaff, M. W.; Schaefer, W. P.; Henling, L.; Labinger, J. A.; Bercaw, J. E.; Gray, H. B. Inorg. Chem. 1995, 34, 3625-3632.
80. Jentzen, W.; Turowska-Tyrk, I.; Scheidt, W. R.; Shelnutt, J. A. Inorg. Chem. 1996, 35, 3559.
81. Marguet, S.; Hapiot, P.; Neta, P. Phys. Chem. 1994, 98, 7136.
82. Ma, J. K.; Mathews, S.; Davidson, V. L. Biochemistry- 2007, 46, 8561.