Supramolecular triad and pentad composed of zinc-porphyrin(s), oxoporphyrinogen, and fullerene(s): Design and electron-transfer studies

Chemistry - A European Journal

Volumn 13, Issue 16, 2007, Pages 4628-4635

  Schumacher, Amy Lea ^a   Sandanayaka, Atula S D ^b   Hill, Jonathan P ^c   Ariga, Katsuhiko ^c   Karr, Paul A ^a   Araki, Yasuyuki ^b   Ito, Osamu ^b   D'Souza, Francis ^a  

^a WICHITA STATE UNIVERSITY   (United States)

^b TOHOKU UNIVERSITY   (Japan)

^c NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

Density functional calculations; Electron transfer; Fullerenes; Porphyrinoids supramolecular chemistry

Indexed keywords

CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; FREE ENERGY; FULLERENES; SUPRAMOLECULAR CHEMISTRY;

ELECTRON TRANSFER; OXOPORPHYRINOGEN; TIME-RESOLVED EMISSION;

PORPHYRINS;

FULLERENE DERIVATIVE; PORPHYRIN; PORPHYRINOGEN; ZINC;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; ELECTRON; INSTRUMENTATION; MACROMOLECULE; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; SENSITIVITY AND SPECIFICITY; SPECTROFLUOROMETRY; TIME; ULTRAVIOLET SPECTROPHOTOMETRY;

ELECTROCHEMISTRY; ELECTRONS; FULLERENES; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PORPHYRINOGENS; PORPHYRINS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; TIME FACTORS; ZINC;

EID: 34250308316     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601854     Document Type: Article

References (73)

1. a) R. A. Marcus, N. Sutin, Biochim. Biophys. Acta 1985, 811, 265;
2. b) R. A. Marcus, Angew. Chem. 1993, 105, 1161;
3. Angew. Chem. Int. Ed. Engl. 1993, 32, 1111;
4. c) M. Bixon, J. Jortner, Adv. Chem. Phys. 1999, 106, 35.
5. a) J. R. Winkler, H. B. Gray, Chem. Rev. 1992, 92, 369;
6. b) C. Kirmaier, D. Holton in The Photosynthetic Reaction Center, Vol. II (Eds.: J. Deisenhofer, J. R. Norris), Academic Press, San Diego,1993, pp. 49-70.
7. a) G. McLendon, R. Hake, Chem. Rev. 1992, 92, 481;
8. b) I. R. Gould, S. Farid, Acc. Chem. Res. 1996, 29, 522;
9. c) N. Mataga, H. Miyasaka, Adv. Chem. Phys. 1999, 107, 431;
10. d) F. D. Lewis, R. L. Letsinger, M. R. Wasielewski, Acc. Chem. Res. 2001, 34, 159.
11. a) J. R. Miller. L. T. Calcaterra, G. L. Closs, J. Am. Chem. Soc. 1984, 106, 3047;
12. b) G. L. Closs, J. R. Miller, Science 1988, 240, 440;
13. c) J. S. Connolly, J. R. Bolton in Photoinduced Electron Transfer, Part D (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam,1988, pp. 303-393.
14. a ) M. R. Wasielewski, Chem. Rev. 1992, 92, 435;
15. b) H. Kurreck, M. Huber, Angew. Chem. 1995, 107, 929;
16. Angew. Chem. Int. Ed. Engl. 1995, 34, 849;
17. c) D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 2001, 34, 40.
18. a) A. Harriman, J.-P. Sauvage, Chem. Soc. Rev. 1996, 25, 41;
19. b) M.-J. Blanco, M. C. Jiménez, J.-C. Chambron, V. Heitz, M. Linke, J.-P. Sauvage, Chem. Soc. Rev. 1999, 28, 293;
20. c) V. Balzani, A. Juris, M. Venturi, S. Campagna, S. Serroni, Chem. Rev. 1996, 96, 759;
21. d) Electron Transfer in Chemistry (Ed.: V. Balzani), Wiley-VCH, Weinheim, 2001.
22. a) M. N. Paddon-Row, Acc. Chem. Res. 1994, 27, 18;
23. b) J. W. Verhoeven, Adv. Chem. Phys. 1999, 106, 603;
24. c) K. Maruyama, A. Osuka, N. Mataga, Pure Appl. Chem. 1994, 66, 867;
25. d) A. Osuka, N. Mataga, T. Okada, Pure Appl. Chem. 1997, 69, 797;
26. e) Molecular Catenanes, Rotaxanes and Knots (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, Weinheim, 1999.
27. a) J. S. Sessler, B. Wang, S. L. Springs, C. T. Brown in Comprehensive Supramolecular Chemistry (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle), Pergamon, Oxford,1996, Chapter 9;
28. b) T. Hayashi, H. Ogoshi, Chem. Soc. Rev. 1997, 26, 355;
29. c) M. W. Ward, Chem. Soc. Rev. 1997, 26, 365.
30. a) Introduction of Molecular Electronics (Eds.: M. C. Petty, M. R. Bryce, D. Bloor), Oxford University Press, New York, 1995;
31. b) Molecular Switches (Ed.: B. L. Feringa), Wiley-VCH, Weinheim, 2001.
32. a) J. S. Connolly, J. R. Bolton in Photoinduced Electron Transfer, Part D (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, pp. 303-393;
33. b) D. M. Guldi, N. Martin, J. Mater. Chem. 2002, 12, 1978;
34. c) L. Sanchez, N. Martin, D. M. Guldi, Angew. Chem. 2005, 117, 5508;
35. Angew. Chem. Int. Ed. 2005, 44, 5374.
36. D. Gust, T. A. Moore in The Porphyrin Handbook, Vol. 8 (Ed.: K. M. Kadish, K. M. Smith, R. Guilard), Academic Press, Burlington, 2000, pp. 153-190.
37. a) K. M. Kadish, R. S. Ruoff, Fullerenes: Chemistry, Physics, and Technology. Wiley-VCH, Weinheim, 2000;
38. b) H. Imahori, Y. Sakata, Adv. Mater. 1997, 9, 537;
39. c) M. Prato, J. Mater. Chem. 1997, 7, 1097;
40. d) N. Martín, L. Sánchez, B. Illescas, I. Pérez, Chem. Rev. 1998, 98, 2527;
41. e) F. Diederich, M. Gómez-López, Chem. Soc. Rev. 1999, 28, 263;
42. f) D. M. Guldi, Chem. Commun. 2000, 321;
43. g) D. M. Guldi, M. Prato, Acc. Chem. Res. 2000, 33, 695;
44. h) D. M. Guldi, Chem. Soc. Rev. 2002, 31, 22;
45. M. D. Meijer, G. P. M. van Klink, G. van Koten, Coord. Chem. Rev. 2002, 230, 141;
46. j) M. E. El-Khouly, O. Ito, P. M. Smith, F. D'Souza, J. Photochem. Photobiol. C 2004, 5, 79;
47. k) H. Imahori, S. Fukuzmi, Adv. Funct. Mater. 2004, 14, 525;
48. F. D'Souza, O. Ito, Coord. Chem. Rev, 2005, 249, 1410;
49. I. Bouamaied, T. Coskun, E. Stulz, Struct. Bonding 2006, 121, 1.
50. a) H. W. Kroto, J. R. Heath, S. C. O'Brien, R. F. Curl, R. E. Smalley, Nature 1985, 318, 162;
51. b) W. Kratschmer, L. D. Lamb, F. Fostiropoulos, D. R. Huffman, Nature 1990, 347, 345.
52. a) Fullerene and Related Structures, Vol. 199 (Ed.; A. Hirsch), Springer, Berlin, 1999;
53. b) Q. Xie, E. Pèrez-Cordero, L. Echegoyen, J. Am. Chem. Soc. 1992, 114, 3978;
54. c) H. Imahori, K. Hagiwara, T. Akiyama, M. Akoi, S. Taniguchi, T. Okada, M. Shirakawa, Y. Sakata. Chem. Phys. Lett. 1996, 263, 545;
55. d) D. M. Guldi, K.-D. Asmus, J. Am. Chem. Soc. 1997, 119, 5744;
56. e) H. Imahori, M. E. ElKhouly, M. Fujitsuka, O. Ito, Y. Sakata, S. Fukuzumi, J. Phys. Chem. A 2001, 105, 325.
57. J. P. Hill, A. S. D. Sandanayaka, A. L. McCarty, P. A. Karr, M. E. Zandler, R. Charvet, K. Ariga, Y. Araki, O. Ito, F. D'Souza, Eur. J. Org. Chem. 2006, 595.
58. F. D'Souza, G. R. Deviprasad, M. E. Zandler, V. T. Hoang, K. Arkady, M. VanStipdonk, A. Perera, M. E. El-Khouly, M. Fujitsuka, O. Ito, J. Phys. Chem. A 2002, 106, 3243.
59. H. A. Benesi, J. H. Hildebrand, J. Am. Chem. Soc. 1949, 71, 2703.
60. a) J. P. Hill, I. J. Hewitt, C. E. Anson, A. K. Powell, A. L. McCarty, P. A. Karr, M. E. Zandler, F. D'Souza, J. Org. Chem. 2004, 69, 5861;
61. b) J. P. Hill, W. Schmitt, A. L. McCarty, K. Ariga, F. D'Souza, Eur. J. Org. Chem. 2005, 2893.
62. a) D. Rehm, A. Weller, Isr. J. Chem. 1970, 8, 259;
63. b) N. Mataga, H. Miyasaka in Electron Transfer, Part 2 (Eds.: J. Jortner, M. Bixon), Wiley, New York, 1999, pp. 431.
64. Gaussian 03, Revision B.04, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong. C. Gonzalez. J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
65. For examples of B3LYP/3-21G(*) applied to porphyrin-fullerene systems, see: M. E. Zandler, F. D'Souza. C. R. Chim. 2006, 9, 960.
66. a) T. Nojiri, A. Watanabe, O. Ito, J. Phys. Chem. A 1998, 102, 5215;
67. b) H. N. Ghosh, H. Pal, A. V. Sapre, J. P. Mittal, J. Am. Chem. Soc. 1993, 115, 11722;
68. c) M. Fujitsuka, O. Ito, T. Yamashiro, Y. Aso, T. Otsubo, J. Phys. Chem. A 2000, 104, 4876;
69. d) F. D'Souza, P. M. Smith, M. E. Zandler, A. L. McCarty, M. Itou, Y. Araki, O. Ito, J. Am. Chem. Soc. 2004, 126, 7898.
70. J. P. Hill, A. L. Schumacher, F. D'Souza, J. Labuta, C. Redshaw, M. J. R. Elsegood, M. Aoyagi, T. Nakanishi, K. Ariga, Inorg. Chem. 2006, 45, 8288.
71. a) K. Matsumoto, M. Fujitsuka, T. Sato, S. Onodera, O. Ito, J. Phys. Chem. B 2000, 104, 11632;
72. b) S. Komamine, M. Fujitsuka, O. Ito, K. Morikawa, T. Miyata, T. Ohno, J. Phys. Chem. A 2000, 104, 11497;
73. c) M. Yamazaki, Y. Araki, M. Fujitsuka, O. Ito, J. Phys. Chem. A 2001, 105, 8615.