Dimeric and trimeric tetrathiafulvalenes with strong intramolecular interactions in the oxidized states

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3122-3125

  Nakamura, Ken Ichi ^a   Takashima, Tsuyoshi ^a   Shirahata, Takashi ^a   Hino, Shojun ^a   Hasegawa, Masashi ^b   Mazaki, Yasuhiro ^b   Misaki, Yohji ^a  

^a EHIME UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79958863643     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol201025g     Document Type: Article

References (37)

1. Saito, G.; Yoshida, Y. Bull. Chem. Soc. Jpn. 2007, 80, 1-137
2. Organic Superconductors (Including Fullerenes); Williams, J. M.; Ferraro, J. R.; Thorn, R. J.; Carlson, D.; Geiser, U.; Wang, H. H.; Kini, A. M.; Whangbo, M. H., Eds.; Prentice Hall: Engelwood Cliffs, 1992.
3. TTF Chemistry: Fundamental and Applications of Tetrathiafulvalene; Yamada, J.; Sugimoto, T., Eds.; Kodansha-Springer: Tokyo, 2004.
4. Special issue on molecular conductors. Batail, P., Ed. Chem. Rev. 2004, 104, 4887-5781.
5. Hasegawa, M.; Iyoda, M. Chem. Soc. Rev. 2010, 39, 2420-2427
6. Amabilino, D. B.; Puigmartí-Luis, J. Soft. Matter 2010, 6, 1605-1612
7. Iyoda, M.; Hasegawa, M.; Miyake, Y. Chem. Rev. 2004, 104, 5085-5113
8. Segura, J. L.; Martín, N. Angew. Chem., Int. Ed. 2001, 40, 1372-1409
9. Canevet, D.; Sallé, M.; Zhang, G.; Zhu, D. Chem. Commun. 2009, 2245-2269
10. Jørgensen, M.; Lerstrup, K. A.; Bechgaard, K. J. Org. Chem. 1991, 56, 5684-5688
11. Sudmale, I. V.; Tormos, G. V.; Khodorkovsky, V. Y.; Edzina, A. S.; Neilands, O. J.; Cava, M. P. J. Org. Chem. 1993, 58, 1355-1358
12. Izuoka, A.; Kumai, R.; Sugawara, T. Chem. Lett. 1992, 285-288
13. Jia, C.; Zhang, D.; Guo, X.; Wan, S.; Xu, W.; Zhu, D. Synthesis 2002, 2177-2182
14. Carcel, C.; Fabre, J.-M.; Bonneval, B. G.; de; Coulon, C. New. J. Chem. 2000, 24, 919-924
15. Spanggaard, H.; Prehn, J; Nielsen, M. B.; Levillain, E.; Allain, M.; Becher, J. J. Am. Chem. Soc. 2000, 122, 9486-9496
16. Fujiwara, H.; Arai, E.; Hayao, K. J. Mater. Chem. 1998, 8, 829-831
17. Iyoda, M.; Hasegawa, M.; Kuwatani, Y.; Nishikawa, H.; Fukami, K.; Nagase, S. Chem. Lett. 2001, 1146-1147
18. Lyskawa, J.; Sallé, M.; Balandier, J. Y.; Derf, F. L.; Levillain, E.; Allain, M.; Viel, P.; Palacin, S. Chem. Commun. 2006, 2233-2235
19. Hasegawa, M.; Kobayashi, Y.; Hara, K.; Enozawa, H.; Iyoda, M. Heterocycles 2009, 77, 837-842
20. Iyoda, M.; Hara, K.; Kuwatani, Y.; Nagase, S. Org. Lett. 2000, 2, 2217-2220
21. Khodorkovsky, V.; Shapiro, L.; Krief, P.; Shames, A.; Mabon, G.; Giard, M. Chem. Commun. 2001, 2736-2737
22. Roskha, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2007, 129, 828-838
23. Hasegawa, M.; Takano, J.; Enozawa, H.; Kuwatani, Y.; Iyoda, M. Tetrahedron Lett. 2004, 45, 4109-4112
24. Hasegawa, M.; Enozawa, H.; Kawabata, Y.; Iyoda, M. J. Am. Chem. Soc. 2007, 129, 3072-3073
25. Ziganshima, A. Z.; Ko, Y. H.; Jeon, W. S.; Kim, K. Chem. Commun. 2004, 806-807
26. Yasuda, T.; Tanabe, K.; Tsuji, T.; Coti, K. K.; Aprahamian, I.; Stoddart, J. F.; Kato, T. Chem. Commun. 2010, 1224-1226
27. Carcel, C.; Fabre, J.-M. Synth. Met. 2002, 130, 99-109
28. Carcel, C.; Fabre, J.-M. Synth. Met. 2001, 120, 747-748
29. Hong, W.; Xu, W.; Wang, Q.; Zhu, D. Synth. Met. 2009, 159, 735-740
30. Svenstrup, N.; Rasmussen, K. M.; Hansen, T. K.; Becher, J. Synthesis 1994, 809-812
31. Simonsen, B.; Svenstrup, N.; Lau, J.; Simonsen, O.; Mork, P.; Kristensen, G. J.; Becher, J. Synthesis 1996, 407-418
32. See the Supporting Information.
33. int = 0.1503). Final R indices [ I > 2σ(I)]: R1 = 0.0777, wR2 = 0.1760, GOF = 0.788.
34. 6+, were applied.
35. •+ in solution.
36. Torrance, J. B.; Scott, B. A.; Welber, B.; Kaufman, F. B.; Seiden, P. E. Phys. Rev. B 1979, 19, 730-741
37. Kozlov, M. E.; Tanaka, Y.; Tokumoto, M.; Tani, T. Synth. Met. 1995, 70, 987-988