Screening electronic communication through ortho-, meta- And para-substituted linkers separating subphthalocyanines and C60

Chemistry - A European Journal

Volumn 14, Issue 25, 2008, Pages 7670-7679

  González Rodríguez, David ^b   Torres, Tomás ^b   Herranz, María Ángeles ^c,d   Echegoyen, Luis ^c   Carbonell, Esther ^a   Guldi, Dirk M ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^c CLEMSON UNIVERSITY   (United States)

^d UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Donor acceptor systems; Electron transfer; Energy transfer; Fullerenes; Subphthalocyanines

Indexed keywords

DONOR-ACCEPTOR SYSTEMS; ELECTRON TRANSFER; ENERGY TRANSFER; FULLERENES; SUBPHTHALOCYANINES;

BORON DERIVATIVE; FULLERENE C60; FULLERENE DERIVATIVE; INDOLE DERIVATIVE; PHTHALOCYANINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; ENERGY TRANSFER; METHODOLOGY; REPRODUCIBILITY; SPECTROFLUOROMETRY; STEREOISOMERISM; SYNTHESIS; TIME; ULTRAVIOLET SPECTROPHOTOMETRY;

BORON COMPOUNDS; ELECTRONS; ENERGY TRANSFER; FULLERENES; INDOLES; MOLECULAR STRUCTURE; REPRODUCIBILITY OF RESULTS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; TIME FACTORS;

EID: 53849114361     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800910     Document Type: Conference Paper

References (79)

1. Electron Transfer in Chemistry, Vol. I-V, (Ed.: V. Balzani), Wiley-VCH, Weinheim, 2001.
2. Molecular Mechanisms of Photosynthesis (Ed.: R. E. Blankenship), Blackwell Science. Oxford, 2002.
3. a) C. Winder, N. S. Sariciftci, J. Mater. Chem. 2004, 14, 1077-1086;
4. b) S. Guenes, H. Neugebauer, N. S. Sariciftci, Chem. Rev. 2007, 107, 1324-1338.
5. a) D. M. Guldi, N. Martin, J. Mater. Chem. 2002, 12, 1978-1992;
6. b) D. M. Guldi, H. Imahori, J. Porphyrins Phthalocyanines 2004, 8, 976-983;
7. c) D. M. Guldi, F. Zerbetto, V. Georgakilas, M. Prato, Acc. Chem. Res. 2005, 38, 38-43;
8. d) D. M. Guldi, G. M.A. Rahman, C. Ehli, V. Sgobba, Chem. Soc. Rev. 2006, 35, 471-487;
9. e) D. M. Guldi, Phys. Chem. Chem. Phys. 2007, 9, 1400-1420.
10. a) J. M. Tour, Chem. Rev. 1996, 96, 537-554;
11. b) M. A. Reed, C. Zhou, C. J. Muller, T. P. Burgin, J. M. Tour, Science 1997, 278, 252-254;
12. c) J. Chen, M. A. Reed, A.M. Rawlett, J.M. Tour, Science 1999, 286, 1550-1552;
13. d) D. K. James, J. M. Tour, Top. Curr. Chem. 2005, 257, 33-62.
14. T. Hayes, M. R. Wasielewski, D. Gosztola, J. Am. Chem. Soc. 2000, 122, 5563-5567.
15. W. B. Davis, W. A. Svec, M.A. Ratner, M. R. Wasielewski, Nature 1998, 396, 60-63.
16. a) M. Sirish, R. Kache, B. G. Maiya, J. Photochem. Photobiol. A 1996, 93, 129-136;
17. b) N. V. Tkachenko, H. Lemmetyinen, J. Sonoda, K. Ohkubo, T. Sato, H. Imahori, S. Fukuzumi, J. Phys. Chem. A 2003, 107, 8834-8844;
18. c) H. Nishikawa, S. Kojima, T. Kodama, I. Ikemoto, S. Susuki, K. Kikuchi, M. Fujitsuka, L. Hongxia, Y. Araki, O. Ito, J. Phys. Chem. A 2004, 108, 1881-1890.
19. a) H. A. Kramers, Physica 1934, 1, 182-192;
20. b) M. Bixon, J. Jortner, M. E. Michel-Beyerle, A. Ogrodnik, Biochim. Biophys. Acta 1989, 977, 273-286.
21. a) D. Gust, T. A. Moore, A. L. Moore, C. Devadoss, P. A. Liddell, R. Hermant, R. A. Nieman, L. J. Demanche, J. M. DeGraziano, I. Gouni, J. Am. Chem. Soc. 1992, 114, 3590-3603;
22. b) A. Harriman, F. M. Romero, R. Ziessel, J. Phys. Chem. A 1999, 103, 5399-5408.
23. a) H. Imahori, K. Hagiwara, M. Aoki, T. Akiyama, S. Taniguchi, T. Okada, M. Shirakawa, Y. Sakata, J. Am. Chem. Soc. 1996, 118, 11771-11782;
24. b) S. Shinoda, H. Tsukube, Y Nishimura, I. Yamazaki, A. Osuka, Tetrahedron 1997, 53, 13657-13666;
25. c) A. Stockmann, J. Kurzawa, N. Fritz, N. Acar, S. Schneider, J. Daub, R. Engl, T. Clark, J. Phys. Chem. A 2002, 106, 7958-7970;
26. d) S. Shaakov, T Galili, E. Stavitski, H. Levanon, A. Lukas, M. R. Wasielewski, J. Am. Chem. Soc. 2003, 125, 6563-6572;
27. e) A. L. Thompson, T.-S. Ahn, K. R. J. Thomas, S. Thayumanavan, T. J. Martinez, C. J. Bardeen, J. Am. Chem. Soc. 2005, 127, 16348-16349.
28. J.J. Sunner, S. E. Creager, J. Am. Chem. Soc. 2000, 122, 11914-11920.
29. a) K. M. Gaab, A. L. Thompson, J. Xu, T. J. Martinez, C. J. Bardeen, J. Am. Chem. Soc. 2003, 125, 9288-9289;
30. b) A. L. Thompson, K. M. Gaab, J. Xu, C. J. Bardeen, T. J. Martinez, J. Phys. Chem. A 2004, 108, 671-682.
31. a) D. E. Richardson, H. Taube, J. Am. Chem. Soc. 1983, 105, 40-51;
32. b) V. Marvaud, J.-P. Launay, C. Joachim, Chem. Phys. 1993, 177, 23-30;
33. c) B. P. Paulson, L. A. Curtiss, B. Bal, G. L. Closs, J. R. Miller, J. Am. Chem. Soc. 1996, 118, 378-387;
34. d) C. Patoux, C. Coudret, J.-P. Launay, C. Joachim, A. Gourdon, Inorg. Chem. 1997, 36, 5037-5049;
35. e) C. Patoux, J.-P. Launay, M. Beley, S. Chodorowsky-Kimmes, J.-P. Collin, S. James, J.-P. Sauvage, J. Am. Chem. Soc. 1998, 120, 3717-3725;
36. f) C. Rovira, D. Ruiz-Molina, O. Eisner, J. Vidal-Gancedo, J. Bonvoisin, J.-P. Launay, J. Veciana, Chem. Eur. J. 2001, 7, 240-250;
37. g) V. Lloveras, J. Vidal-Gancedo, D. Ruiz-Molina, T. M. Figueira-Duarte, J.-F. Nierengarten, J. Veciana, C. Rovira, Faraday Discuss. 2006, 131, 291-305.
38. a) A. Meller, A. Ossko, Monatsh. Chem. 1972, 103, 150-155;
39. seminal work in this area was done by N. Kobayashi, see, for example: b) N. Kobayashi, R. Kondo, S. Nakajima, T. Osa, J. Am. Chem. Soc. 1990, 112, 9640-9641;
40. relevam reviews can be found in: c) M. Geyer, F. Plenzig, J. Rauschnabel, M. Hanack, B. del Rey, A. Sastre, T. Torres, Synthesis 1996, 1139;
41. d) C. G. Claessens, D. González-Rodríguez, T. Torres, Chem. Rev. 2002, 102, 835-853;
42. e) "Synthesis and Spectroscopic Properties of Phthalocyanine Analogs": N. Kobayashi, in The Porphyrin Handbook Vol. 15, (Eds.: K.M. Kadish, K.M. Smith, R. Guilard), Academic Press, San Diego. CA, 2003, pp. 161-262;
43. f) T. Torres, Angew. Chem. 2006, 118, 2900-2903;
44. Angew. Chem. Int. Ed. 2006, 45, 2834-2837;
45. g) G. de la Torre, C. G. Claessens, T. Torres, Chem. Commun. 2007, 2000-2015.
46. a) N. Kobayashi, T. Ishizaki, K. Ishii, K. Konami, J. Am. Chem. Soc. 1999, 121, 9096-9110;
47. b) C. G. Claessens, T. Torres, Tetrahedron Lett. 2000, 41, 6361-6365;
48. c) C. G. Claessens, T. Torres, Angew. Chem. 2002, 114, 2673-2677;
49. Angew. Chem. Int. Ed. 2002, 41, 2561-2565;
50. d) T. Fukuda, J. R. Stork, R. J. Potucek, M. M. Olmstead, B. C. Noll, N. Kobayashi, W. S. Durfee. Angew. Chem. 2002, 114, 2677-2680;
51. Angew. Chem. Int. Ed. 2002, 41, 2565-2568;
52. for nonlinear optical properties see: e) A. Sastre, T. Torres, M.A. Díaz-García, F. Agulló-López, C. Dhenaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc,. 1996, 118, 2746-2747;
53. f) B. del Rey, U. Keller, T. Torres, G. Rojo, F. Agulló- López, S. Nonell, C. Martí, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1998, 120, 12808-12817;
54. g) G. de la Torre, P. Vázquez, F. Agulló-López, T. Torres, J. Mater. Chem. 1998, 8, 1671-1683;
55. h) G. de la Torre, P. Vázquez, F. Agulló-López, T. Torres, Chem. Rev. 2004, 104, 3723-3750.
56. SubPcs are the subject of increasing attention as electron and/or energy donors/acceptors in molecular systems, a) D. González-Rodríguez, T. Torres, D. M. Guldi, J. Rivera, L. Echegoyen, Org. Lett. 2002, 4, 335-338;
57. b) D. González-Rodríguez, T. Torres, M.A. Herranz, J. Rivera, L. Echegoyen, D. M. Guldi, J. Am. Chem. Soc. 2004, 126, 6301-6313;
58. c) D. González-Rodríguez, C.G. Claessens, T. Torres, S. Liu, L. Echegoyen, N. Vila, S. Nonell, Chem. Eur. J. 2005, 11, 3881-3893;
59. d) D. González-Rodríguez, T. Torres, M. M. Olmstead, J. Rivera, M.A. Herranz, L. Echegoyen, C. Atienza Castella-nos, D.M. Guldi, J. Am. Chem. Soc. 2006, 128, 10680-10681;
60. e) R. S. Iglesias, C. G. Claessens, G. M.A. Rahman, M.A. Herranz, D. M. Guldi, T. Torres, Tetrahedron 2007, 63, 12396-12404;
61. f) M. E. El-Khouly, S. H. Shim, Y. Araki, O. Ito, K.-Y. Kay, J. Phys. Chem. B 2008, 112, 3910-3917;
62. g) A. Medina, C.G. Claessens, G. M. A. Rahman, A. M. Lamsabhi, O. Mo, M. Yañez, D. M. Guldi, T. Torres, Chem. Commun. 2008, 1759-1761.
63. a) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177;
64. Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
65. b) B. H. Yang, S. L. Buchwald, J. Organomet. Chem. 1999, 576, 125-146.
66. C.G. Claessens, D. González-Rodríguez, B. del Rey, T. Torres, G. Mark, H.-P. Schuchmann, C. von Sonntag, J. G. MacDonald, R. S. Nohr, Eur. J. Org. Chem. 2003, 2547-2551.
67. a) M. Prato, M. Maggini, Acc. Chem. Res. 1998, 31, 519-526;
68. b) N. Tagmatarchis, M. Prato, Synlett 2003, 6, 768-779.
69. 60 unsaturated sphere; see: A. L. Balch, M. M. Olmstead. Chem. Rev. 1998, 98, 2123-2165.
70. 1 regioisomers, due to their almost identical physical properties.
71. Structural modeling was performed using the Hyperchem 6.03 package (Hypercube, Inc.) for Windows.
72. Detection of the subphthalocyanine fluorescence was hampered in some cases (dyads 1a) by the instrumental time resolution (< 100 ps).
73. 60 component was seen in o-1b, m-1b, and p- 1b.
74. a) D. M. Guldi, Pure Appl. Chem. 2003, 75, 1069-1075;
75. b) H. Imahori, Org. Biomol. Chem. 2004, 2, 1425-1433;
76. c) S. Fukuzumi, Funct. Org. Mater. 2007, 465-510.
77. a) D. M. Guldi, A. Gouloumis, P. Vázquez, T. Torres, V. Georgakilas, M. Prato, J. Am. Chem. Soc. 2005, 127, 5811-5813;
78. b) M. Quintiliani, A. Kahnt, T. Wölfle, W. Hieringer, P. Vázquez, A. Görling, D. M. Guldi, T. Torres, Chem. Eur. J. 2008, 14, 3765-3775.
79. Notable is, nevertheless, that the charge recombination is not quantitative. For example, at the end of the femtosecond timescale a residual absorbance persists that lasts well into the nanosecond regime. The overall yield of this long-lived product is about 10%.