Photoinduced energy-transfer and electron-transfer processes in molecules of tetrakis((E)-2-(50-hexyl-2,20-bithiophen-5-yl)vinyl)benzene and perylenediimide

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 218, Issue 1, 2011, Pages 17-25

  El Khouly, Mohamed E ^a,b   Choi, Dong Hoon ^c   Fukuzumi, Shunichi ^a,d  

^a OSAKA UNIVERSITY   (Japan)

^b Kafrelsheikh University   (Egypt)

^c Korea University   (South Korea)

^d Ewha Womans University   (South Korea)

Author keywords

Electron transfer; Energy transfer; Oligothiophene; Perylenediimide

Indexed keywords

EID: 79551529821     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.11.018     Document Type: Article

References (67)

1. R.E. Blankenship, Molecular Mechanisms of Photosynthesis 2002 Blackwell Science Oxford, U.K.
2. T. Brixner, J. Stenger, H.M. Vaswani, M. Cho, R.E. Blankenship, and G.R. Fleming Nature 434 2005 625
3. B.A. Heller, D. Holten, and C. Kirmaier Science 269 1995 940
4. M.R. Wasielewski Chem. Rev. 92 1992 435
5. A.F. Collings, C. Critchley, Artificial Photosynthesis, from Basic Biology to Industrial Application 2005 Wiley-VCH Weinheim
6. D. Gust, T.A. Moore, and A.L. Moore Acc. Chem. Res. 42 2009 1890
7. H. Imahori, D.M. Guldi, K. Tamaki, Y. Yoshida, C. Luo, Y. Sakata, and S. Fukuzumi J. Am. Chem. Soc. 123 2001 6617
8. C.J. Brabec, N.S. Sariciftci, and J.C. Hummelen Adv. Funct. Mater. 11 2001 15
9. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, and A.J. Heeger Science 270 1995 1789
10. M.C. Petty, M.R. Bryce, D. Bloor, Introduction of Molecular Electronics 1995 Oxford University Press New York 2001
11. M. Granstrom, K. Petrisch, A.C. Arias, A. Lux, M.R. Andersson, and R.H. Friend Nature 395 1998 257
12. J.J.M. Halls, C.A. Walsh, N.C. Greenham, E.A. Marseglia, R.H. Friend, S.C. Moratti, and A.B. Holmes Nature 376 1995 498
13. D. Chirvase, J. Parisi, J.C. Hummelen, and V. Dyakonov Nanotechnology 15 2004 1317
14. C.D. Dimitrakopoulos, and P.R.L. Malenfant Adv. Mater. 14 2002 99
15. R.D. Costa, F.J. Céspedes-Guirao, E. Ortí, H.J. Bolink, J. Gierschner, F. Fernández-Lázaro, and A. Sastre-Santos Chem. Commun. 2009 3886
16. R.H. Goldsmith, L.E. Sinks, R.F. Kelley, L.J. Betzen, W. Liu, E.A. Weiss, M.A. Ratner, and M.R. Wasielewski Proc. Natl. Acad. Sci. 102 2005 3540
17. B.K. Kaletas, R. Dobrawa, A. Sautter, F. Würthner, M. Zimine, L. De Cola, and R.M. Williams J. Phys. Chem. A 108 2004 1900
18. L. Flamigni, B. Ventura, C.-C. You, C. Hippius, and F. Würthner J. Phys. Chem. C 111 2007 622
19. S. Xiao, M.E. El-Khouly, Y. Li, Z. Gan, H. Liu, L. Jiang, Y. Araki, O. Ito, and D. Zhu J. Phys. Chem. B 109 2005 3658
20. W. Seitz, A.J.S. Jimenez, E. Carbonell, B. Grimm, M.S. Rodriguez-Morgade, D.M. Guldi, and T. Torres Chem. Commun. 46 2010 127
21. E.H.A. Beckers, Z. Chen, S.C.J. Meskers, P. Jonkheijm, A.P.H.J. Schenning, X.-Q. Li, P. Osswald, F. Würthner, and R.A.J. Janssen J. Phys. Chem. B 110 2006 16967
22. U. Hahn, S. Engmann, C. Oelsner, C. Ehli, D.M. Guldi, and T. Torres J. Am. Chem. Soc. 132 2010 6392
23. C.-C. You, P. Espindola, C. Hippius, J. Heinze, and F. Würthner Adv. Funct. Mater. 17 2007 3764
24. S. Fukuzumi, K. Ohkubo, J. Ortiz, A.M. Gutiérrez, F. Fernández-Lázaro, and Á. Sastre-Santos J. Phys. Chem. A 112 2008 10744
25. F.J. Céspedes-Guirao, K. Ohkubo, S. Fukuzumi, Á. Sastre-Santos, and F. Fernández-Lázaro J. Org. Chem. 74 2009 5871
26. H. Zollinger, Color Chemistry 3rd ed. 2003 VCH Weinheim, Germany
27. C. Li, M. Liu, N.G. Pschirer, M. Baumgarten, and K. Müllen Chem. Rev. 110 2010 6817
28. J. Li, F. Dierschke, J. Wu, A.C. Grimsdale, and K. Muüllen J. Mater. Chem. 16 2006 96
29. R. de Bettignies, Y. Nicolas, P. Blanchard, E. Levillain, J.M. Nunzi, and J. Roncali Adv. Mater. 15 2003 1939
30. L. Schmidt-Mende, A. Fechtenkotter, K. Müllen, E. Moons, R.H. Friend, and J.D. MacKenzie Science 293 2001 1119
31. R.F. Kelley, W.S. Shin, B. Rybtchinski, L.E. Sinks, and M.R. Wasielewski J. Am. Chem. Soc. 129 2007 3173
32. P. Osswald, and F. Würthner Chem. Eur. J. 13 2007 7395
33. T.E. Kaiser, H. Wang, V. Stepanenko, and F. Würthner Angew. Chem. Int. Ed. 46 2007 5541
34. R. Schmidt, M.M. Ling, J.H. Oh, M. Winkler, M. Könemann, Z. Bao, and F. Würthner Adv. Mater. 19 2007 3692
35. J.H. Oh, S. Liu, Z. Bao, R. Schmidt, and F. Würthner Appl. Phys. Lett. 91 2007 212107
36. P. Jonkheijm, N. Stutzmann, Z. Chen, D.M. de Leeuw, E.W. Meijer, A.P.H.J. Schenning, and F. Würthner J. Am. Chem. Soc. 128 2006 9535
37. A. Mishra, C-Q. Ma, and P. Bäuerle Chem. Rev. 109 2009 1141
38. D. Fichou, Handbook of Oligo- and Polythiophenes 1999 Wiley-VCH Weinheim
39. P. Bäuerle, K. Müllen, G. Wegener, Electronic Materials: The Oligomer Approach 1998 Wiley-VCH Weinheim
40. I.F. Perepichka, D.F. Perepichka, H. Meng, and F. Wudl Adv. Mater. 17 2005 2281
41. B.J. Holliday, and T.M. Swager Chem. Commun. 2005 23
42. H. Rockel, J. Huber, R. Gleiter, and W. Schuhmann Adv. Mater. 6 1994 568
43. D.M. Welsh, A. Kumar, E.W. Meijer, and J.R. Reynolds Adv. Mater. 11 1999 1379
44. E. Mena-Osteritz, and P. Bäuerle Adv. Mater. 18 2006 447
45. F. Jäckel, M.D. Watson, K. Müllen, and J.P. Rabe Phys. Rev. Lett. 92 2004 188303
46. T. Benincori, V. Bonometti, F. De Angelis, L. Falciola, M. Muccini, P.R. Mussini, T. Pilati, G. Rampinini, S. Rizzo, S. Toffanin, and F. Sannicol Chem. Eur. J. 16 2010 9086
47. J. Cremer, and P. Bäuerle Eur. J. Org. Chem. 2005 3715
48. J.L. Segura, R. Gomez, R. Blanco, E. Reinold, and P. Baäuerle Chem. Mater. 18 2006 2834
49. J. Cremer, and P. Bäuerle J. Mater. Chem. 16 2006 874
50. J. Cremer, E. Mena-Osteritz, N.G. Pschierer, K. Müllen, and P. Bäuerle Org. Biomol. Chem. 3 2005 985
51. C.-Q. Ma, E. Mena-Osteritz, T. Debaerdemaeker, M.M. Wienk, R.A. Janssen, and P. Baäeuerle Angew. Chem. Int. Ed. 46 2007 1679
52. X. Zhan, Z. Tan, B. Domercq, Z. An, X. Zhang, S. Barlow, Y. Li, D. Zhu, B. Kippelen, and S.R. Marder J. Am. Chem. Soc. 129 2007 7246
53. Y. Ie, T. Uto, N. Yamamoto, and Y. Aso Chem. Commun. 2009 1213
54. M.H. Kim, M.J. Cho, K.H. Kim, M.H. Hoang, T.W. Lee, J.-I. Jin, N.S. Kang, J.-W. Yu, and D.H. Choi Org. Electron. 10 2009 1429
55. M. Fujitsuka, K. Harada, A. Sugimoto, and T. Majima J. Phys. Chem. A 112 2008 10193
56. M.K.R. Fischer, T.E. Kaiser, F. Würthner, and P. Baäuerle J. Mater. Chem. 19 2009 1129
57. E.H.A. Beckers, S.C.J. Meskers, A.P.H.J. Schenning, Z. Chen, F. Würthner, and R.A.J. Janssen J. Phys. Chem. A 108 2004 6933
58. M. Jaggi, C. Blum, B.S. Marti, S.-X. Liu, S. Leutwyler, and S. Decurtins Org. Lett. 12 2010 1344
59. L.X. Chen, S. Xiao, and L. Yu J. Phys. Chem. B 110 2006 11738
60. N. Mataga, and H. Miyasaka J. Jortner, M. Bixon, In Electron Transfer 1999 John Wiley & Sons New York 431 496 Part 2
61. B.R. Arnold, S. Farid, J.L. Goodman, and I.R. Gould J. Am. Chem. Soc. 118 1996 5482
62. M. Supur, M.E. El-Khouly, J.H. Seok, J.H. Kim, K.-Y. Kay, and S. Fukuzumi J. Phys. Chem. C 114 2010 10969
63. G.J. Kavarnos, Fundamental of Photoinduced Electron Transfer 1993 VCH Publishers, Inc. New York
64. f0 is the lifetime of the PDI reference (6.0 ns).
65. J.R. Lakowicz, Principles of Fluorescence Spectroscopy 2nd ed. 1999 Kluwer Academic/Plenum Publishers New York
66. T. Förster Ann. Phys. 55 1948
67. L. Stryer, and R.P. Haugland Proc. Natl. Acad. Sci. U.S.A. 1967 719