Abstract
As an alternative to conventional charge-separation functional molecular models based on multi-step long-range electron transfer (ET) within redox cascades, simple donor-acceptor dyads have been developed to attain a long-lived and high-energy charge-separated (CS) state without significant loss of excitation energy. In particular, a simple molecular electron donor-acceptor dyad, 9-mesityl-10-methylacridinium ion (Acr+-Mes), is capable of fast charge separation but extremely slow charge recombination. Such a simple molecular dyad has significant advantages with regard to synthetic feasibility, providing a variety of applications for photoinduced ET catalytic systems, including efficient photocatalytic systems for the solar energy conversion and construction of organic solar cells.
Conference
IUPAC International Conference on Physical Organic Chemistry (ICPOC-18), International Conference on Physical Organic Chemistry, ICPOC, Physical Organic Chemistry, 18th, Warsaw, Poland, 2006-08-20–2006-08-25
References
1. doi:10.1016/S0969-2126(94)00094-8, U. Ermler, G. Fritzsch, S. K. Buchanan, H. Michel. Structure 2, 925 (1994).Search in Google Scholar
2. doi:10.1126/science.245.4925.1463, J. Deisenhofer, H. Michel. Science 245, 1463 (1989).Search in Google Scholar
3. (a) doi:10.1021/ar00028a010, D. Gust, T. A. Moore, A. L. Moore. Acc. Chem. Res. 26, 198 (1993);Search in Google Scholar
3. (b) doi:10.1021/ar9801301, D. Gust, T. A. Moore, A. L. Moore. Acc. Chem. Res. 34, 40 (2001).Search in Google Scholar
4. doi:10.1021/cr00011a005, M. R. Wasielewski. Chem. Rev. 92, 435 (1992).Search in Google Scholar
5. (a) doi:10.1021/ar00037a003, M. N. Paddon-Row. Acc. Chem. Res. 17, 18 (1994);Search in Google Scholar
5. (b) doi:10.1021/cr00011a003, K. D. Jordan, M. N. Paddon-Row. Chem. Rev. 92, 395 (1992).Search in Google Scholar
6. doi:10.1039/a901205b, M.-J. Blanco, M. C. Jimenez, J.-C. Chambron, V. Heitz, M. Linke, J.-P. Sauvage. Chem. Soc. Rev. 28, 293 (1999).Search in Google Scholar
7. (a) S. Fukuzumi, H. Imahori. In Electron Transfer in Chemistry, Vol. 2, V. Balzani (Ed.), pp. 927-975, Wiley-VCH, Weinheim (2001);10.1002/9783527618248.ch31Search in Google Scholar
7. (b) S. Fukuzumi, D. M. Guldi. In Electron Transfer in Chemistry, Vol. 2, V. Balzani (Ed.), pp. 270-337, Wiley-VCH, Weinheim (2001).10.1002/9783527618248.ch19Search in Google Scholar
8. S. Fukuzumi, H. Imahori. In Photochemistry of Organic Molecules in Isotropic and Anisotropic Media, V. Ramamurthy, K. S. Schanze (Eds.), pp. 227-273, Marcel Dekker, New York (2003).Search in Google Scholar
9. D. M. Guldi, S. Fukuzumi. Fullerenes: From Synthesis to Optoelectronic Properties, D. M. Guldi, N. Martin (Eds.), pp. 237-265, Kluwer, Dordrecht (2003).10.1007/978-94-015-9902-3_8Search in Google Scholar
10. (a) doi:10.1039/b300053b, S. Fukuzumi. Org. Biomol. Chem. 1, 609 (2003);Search in Google Scholar
10. (b) doi:10.1246/bcsj.79.177, S. Fukuzumi. Bull. Chem. Soc. Jpn. 79, 177 (2006).Search in Google Scholar
11. doi:10.1021/ja003346i, H. Imahori, K. Tamaki, D. M. Guldi, C. Luo, M. Fujitsuka, O. Ito, Y. Sakata, S. Fukuzumi. J. Am. Chem. Soc. 123, 2607 (2001).Search in Google Scholar
12. doi:10.1021/ja004123v, H. Imahori, D. M. Guldi, K. Tamaki, Y. Yoshida, C. Luo, Y. Sakata, S. Fukuzumi. J. Am. Chem. Soc. 123, 6617 (2001).Search in Google Scholar
13. doi:10.1021/ja016655x, H. Imahori, K. Tamaki, Y. Araki, Y. Sekiguchi, O. Ito, Y. Sakata, S. Fukuzumi. J. Am. Chem. Soc. 124, 5165 (2002).Search in Google Scholar
14. doi:10.1021/ja002052u, S. Fukuzumi, H. Imahori, H. Yamada, M. E. El-Khouly, M. Fujitsuka, O. Ito, D. M. Guldi. J. Am. Chem. Soc. 123, 2571 (2001).Search in Google Scholar
15. doi:10.1002/chem.200305308, H. Imahori, Y. Sekiguchi, Y. Kashiwagi, T. Sato, Y. Araki, O. Ito, H. Yamada, S. Fukuzumi. Chem. Eur. J. 10, 3184 (2004).Search in Google Scholar
16. doi:10.1021/jp036382n, D. M. Guldi, H. Imahori, K. Tamaki, Y. Kashiwagi, H. Yamada, Y. Sakata, S. Fukuzumi. J. Phys. Chem. A 108, 541 (2004).Search in Google Scholar
17. doi:10.1002/anie.199311113, R. A. Marcus. Angew. Chem., Int. Ed. Engl. 32, 1111 (1993).Search in Google Scholar
18. doi:10.1021/ja015738a, S. Fukuzumi, K. Ohkubo, H. Imahori, J. Shao, Z. Ou, G. Zheng, Y. Chen, R. K. Pandey, M.Fujitsuka, O. Ito, K. M. Kadish. J. Am. Chem. Soc. 123, 10676 (2001).Search in Google Scholar
19. doi:10.1021/jp050352y, K. Okamoto, S. Fukuzumi. J. Phys. Chem. B 109,7713 (2005).Search in Google Scholar
20. doi:10.1021/ol0349256, Y. Kashiwagi, K. Ohkubo, J. A. McDonald, I. M. Blake, M. J. Crossley, Y. Araki, O. Ito, H.Imahori, S. Fukuzumi. Org. Lett. 5, 2719 (2003).Search in Google Scholar
21. doi:10.1002/chem.200305239, K. Okamoto, Y. Mori, H. Yamada, H. Imahori, S. Fukuzumi. Chem. Eur. J. 10, 474 (2004).Search in Google Scholar
22. doi:10.1039/b506412k, S. Fukuzumi, K. Ohkubo, J. Ortiz, A. M. Gutierrez, F. Fernandez-Lazarp, A. Sastre-Santos. Chem. Commun. 3814 (2005).Search in Google Scholar
23. doi:10.1021/ja037214b, S. Fukuzumi, K. Ohkubo, W. E. Z. Ou, J. Shao, K. M. Kadish, J. A. Hutchison, K. P. Ghiggino, P. J. Sintic, M. J. Crossley. J. Am. Chem. Soc. 125, 14984 (2003).Search in Google Scholar
24. doi:10.1021/jp026603+, K. Ohkubo, H. Imahori, J. Shao, Z. Ou, K. M. Kadish, Y. Chen, G. Zheng, R. K. Pandey, M. Fujitsuka, O. Ito, S. Fukuzumi. J. Phys. Chem. A 106, 10991 (2002).Search in Google Scholar
25. doi:10.1002/anie.200352870, K. Ohkubo, H. Kotani, J. Shao, Z. Ou, K. M. Kadish, G. Li, R. K. Pandey, M. Fujitsuka, O. Ito, H. Imahori, S. Fukuzumi. Angew. Chem., Int. Ed. 43, 853 (2004).Search in Google Scholar
26. (a) J.-M. Lehn. Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim (1995);10.1002/3527607439Search in Google Scholar
26. (b) J. L. Sessler, B. Wang, S. L. Springs, C. T. Brown. In Comprehensive Supramolecular Chemistry, J. L. Atwood, J. E. D. Davies (Eds.), Elsevier, Oxford (1996).Search in Google Scholar
27. C. J. Chang, J. D. K. Brown, M. C. Y. Chang, E. A. Baker, D. G. Nocera. In Electron Transfer in Chemistry, Vol. 3, V. Balzani (Ed.), pp. 409-461, Wiley-VCH, Weinheim (2001).10.1002/9783527618248.ch41Search in Google Scholar
28. doi:10.1021/ja064678b, M. Tanaka, K. Ohkubo, C. P. Gros, R. Guilard, S. Fukuzumi. J. Am. Chem. Soc. 128, 14625 (2006).Search in Google Scholar
29. doi:10.1021/ja004311l, S. Fukuzumi, K. Ohkubo, T. Suenobu, K. Kato, M. Fujitsuka, O. Ito. J. Am. Chem. Soc. 123, 8459 (2001).Search in Google Scholar
30. doi:10.1021/ja038656q, S. Fukuzumi, H. Kotani, K. Ohkubo, S. Ogo, N. V. Tkachenko, H. Lemmetyinen. J. Am. Chem. Soc. 126, 1600 (2004).Search in Google Scholar
31. H. Kotani, K. Ohkubo, S. Fukuzumi. Chem. Commun. 4520 (2005).Search in Google Scholar
32. doi:10.1002/anie.200301762, A. Harriman. Angew. Chem., Int. Ed. 43, 4985 (2004).Search in Google Scholar
33. (a) doi:10.1039/b501262g, A. C. Benniston, A. Harriman, P. Li, J. P. Rostron, J. W. Verhoeven. Chem. Commun. 2701 (2005);Search in Google Scholar
33. (b) doi:10.1021/ja052967e, A. C. Benniston, A. Harriman, P. Li, J. P. Rostron, H. J. van Ramesdonk, M. M. Groeneveld, H. Zhang, J. W. Verhoeven. J. Am. Chem. Soc. 127, 16054 (2005).Search in Google Scholar
34. doi:10.1021/ja048353b, H. Kotani, K. Ohkubo, S. Fukuzumi. J. Am. Chem. Soc. 126, 15999 (2004).Search in Google Scholar
35. A. A. Frimer. Singlet Oxygen, Vol. 2: Reaction Modes and Products, Part I, CRC Press, Boca Raton (1985).Search in Google Scholar
36. doi:10.1021/ja00820a056, P. A. Burns, C. S. Foote. J. Am. Chem. Soc. 96, 4339 (1974).Search in Google Scholar
37. doi:10.1021/ol051696+, K. Ohkubo, T. Nanjo, S. Fukuzumi. Org. Lett. 7, 4265 (2005).Search in Google Scholar
38. doi:10.1246/bcsj.79.1489, K. Ohkubo, T. Nanjo, S. Fukuzumi. Bull. Chem. Soc. Jpn. 79, 1489 (2006).Search in Google Scholar
39. doi:10.1039/b601418f, K. Ohkubo, K. Yukimoto, S. Fukuzumi. Chem. Commun. 2504 (2006).Search in Google Scholar
40. doi:10.1021/jp065215v, H. Kotani, K. Ohkubo, Y. Takai, S. Fukuzumi. J. Phys. Chem. B 110, 24047 (2006).Search in Google Scholar
41. S. Fukuzumi, T. Tanaka. In Photoinduced Electron Transfer, M. A. Fox, M. Chanon (Eds.), Part C, Chap. 10, Elsevier, Amsterdam (1988).Search in Google Scholar
42. doi:10.1021/ja00236a003, S. Fukuzumi, S. Koumitsu, K. Hironaka, T. Tanaka. J. Am. Chem. Soc. 109, 305 (1987).Search in Google Scholar
43. (a) doi:10.1021/cr00033a003, A. Hagfeldt, M. Gratzel. Chem. Rev. 95, 49 (1995);Search in Google Scholar
43. (b) doi:10.1021/ar980112j, A. Hagfeldt, M. Gratzel. Acc. Chem. Res. 33, 269 (2000);Search in Google Scholar
43. (c) doi:10.1038/35104607, M. Gratzel. Nature 414, 338 (2001).Search in Google Scholar
44. doi:10.1039/a803991g, C. A. Bignozzi, R. Argazzi, C. J. Kleverlaan. Chem. Soc. Rev. 29, 87 (2000).Search in Google Scholar
45. doi:10.1021/ol048913b, T. Hasobe, S. Hattori, H. Kotani, K. Ohkubo, K. Hosomizu, H. Imahori, P. V. Kamat, S.Fukuzumi. Org. Lett. 6, 3103 (2004).Search in Google Scholar
46. doi:10.1039/b413336f, T. Hasobe, S. Hattori, P. V. Kamat, Y. Wada, S. Fukuzumi. J. Mater. Chem. 15, 372 (2005).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston
