Synthesis and π-amphoteric properties of tris(tetrathiafulvaleno) hexadehydro[12]annulene

Heterocycles

Volumn 80, Issue 2, 2010, Pages 909-915

  Hara, Kenji ^a,b   Hasegawa, Masashi ^a,c   Kuwatani, Yoshiyuki ^a,d   Enozawa, Hideo ^a,e   Iyoda, Masahiko ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

^b ADEKA CORPORATION   (Japan)

^c KITASATO UNIVERSITY   (Japan)

^d VSN Inc   (Japan)

^e Institute of Physical and Chemical Research   (Japan)

Author keywords

Interaction; Annulene; Cation Radical; Redox Behavior; Tetrathiafulvalene

Indexed keywords

EID: 77951834710     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-09-S(S)122     Document Type: Article

References (33)

1. R.H. Baughman, H. Eckhardt, and M. Kertesz J. Chem. Phys. 87 1987 6687
2. W.J. Youngs, C.A. Tessier, and J.D. Bradshaw Chem. Rev. 99 1999 3153
3. M. Iyoda, A. Vorasingha, Y. Kuwatani, and M. Yoshida Tetrahedron Lett. 39 1998 4701
4. M. Iyoda, K. Fuchigami, A. Kusaka, T. Yoshida, M. Yoshida, H. Matsuyama, and Y. Kuwatani Chem. Lett. 2000 860
5. S. Sirinintasak, Y. Kuwatani, S. Hoshi, E. Isomura, T. Nishinaga, and M. Iyoda Tetrahedron Lett. 48 2007 3433
6. M. Ohkoshi, T. Horino, M. Yoshida, and M. Iyoda Chem. Commun. 2003 2586
7. K. Hara, M. Hasegawa, Y. Kuwatani, H. Enozawa, and M. Iyoda Chem. Commun. 2004 2042
8. For the TTF oligomers, see M. Iyoda, M. Hasegawa, and Y. Miyake Chem. Rev. 104 2004 5085
9. M. Iyoda, M. Hasegawa, and H. Enozawa Chem. Lett. 36 2007 1402
10. M. Hasegawa, H. Enozawa, and M. Iyoda J. Synth. Org. Chem. Jpn. 66 2008 1211
11. I.D. Campbell, G. Eglinton, W. Henderson, and R.A. Raphael J. Chem. Soc., Chem. Commun. 1966 87
12. D. Solooki, J.D. Ferrara, D. Malaba, J.D. Bradshaw, C.A. Tessier, and W.J. Youngs Inorg. Synth. 31 1997 122
13. C. Huynh, and G. Linstrumelle Tetrahedron 44 1988 6337
14. H.A. Staab, and F. Graf Chem. Ber. 103 1970 1107
15. K.P.C. Vollhardt, and G.D. Whitener Synlett 2003 29
16. M. Iyoda, S. Sirinintasak, Y. Nishiyama, A. Vorasingha, F. Sultana, K. Nakao, Y. Kuwatani, H. Matsuyama, M. Yoshida, and Y. Miyake Synthesis 2004 1527
17. 18: C, 47.72; H, 4.51. Found: C, 47.61; H, 4.58.
18. 1 < TBA, reflecting the decrease in the degree of cyclic conjugation, see: M. Iyoda, Y. Onishi, and M. Nakagawa Tetrahedron Lett. 22 1981 3645
19. 7a
20. 3, see: M. Iyoda, M. Hasegawa, Y. Kuwatani, H. Nishikawa, K. Fukami, S. Nagase, and G. Yamamoto Chem Lett. 2001 1146
21. 3+) in solution. For the formation of a mixed valence dimer from the tris-TTF system, see: M. Hasegawa, J. Takano, H. Enozawa, Y. Kuwatani, and M. Iyoda Tetrahedron Lett. 45 2004 4109
22. M. Iyoda, K. Hara, Y. Kuwatani, and S. Nagase Org. Lett. 2 2000 2217
23. M. Iyoda, M. Hasegawa, K. Hara, J. Takano, E. Ogura, and Y. Kuwatani J. Phys. IV France 114 2004 455
24. M. Hasegawa, Y. Kuwatani, and M. Iyoda J. Phys. IV France 114 2004 505
25. M. Hasegawa, H. Enozawa, Y. Kawabata, and M. Iyoda J. Am. Chem. Soc. 129 2007 3072
26. M. Hasegawa, Y. Kobayashi, K. Hara, H. Enozawa, and M. Iyoda Heterocycles 77 2009 837
27. 19 see: M. Iyoda, M. Hasegawa, J. Takano, K. Hara, and Y. Kuwatani Chem. Lett. 2002 590
28. M. Iyoda, H. Enozawa, and Y. Miyake Chem. Lett. 2004 1098
29. H. Enozawa, M. Hasegawa, D. Takamatsu, K. Fukui, and M. Iyoda Org. Lett. 8 2006 1917
30. H. Enozawa, M. Hasegawa, E. Isomura, T. Nishinaga, T. Kato, M. Yamato, T. Kimura, and M. Iyoda, ChemPhysChem, in press [DOI: 10.1002/cphc.200900545].
31. Although terminal benzene rings of helicenes tend to stack on top of each other, terminal biphenylene rings of heliphenes tend to separate from each other, see: S. Han, D.R. Anderson, A.D. Bond, H.V. Chu, R.L. Disch, D. Holmes, J.M. Schulman, S.J. Teat, K.P.C. Vollhardt, and G.D. Whitener Angew. Chem. Int. Ed. 41 2002 3227
32. J.B. Torrance, B.A. Scott, B. Weiber, F.B. Kaufman, and P.E. Seiden Phys. Rev. B 19 1979 730
33. M.E. Kozlov, Y. Tanaka, M. Tokumoto, and T. Tani Synth. Metal. 70 1995 987