Synthesis and redox behavior of Wurster blue cyclophanes

European Journal of Organic Chemistry

Volumn , Issue 23, 2004, Pages 4936-4941

  Takemura, Hiroyuki ^a   Takehara, Kô ^a   Ata, Masafumi ^a,b  

^a KYUSHU UNIVERSITY   (Japan)

^b SONY CORPORATION   (Japan)

Author keywords

CT complex; Cyclic voltammetry; Cyclophane; Wurster blue radical

Indexed keywords

CARBENE; CYCLOPHANE; PHENYLENEDIAMINE; RADICAL; UNCLASSIFIED DRUG; WURSTER BLUE CYCLOPHANE;

ARTICLE; CYCLIC POTENTIOMETRY; ELECTRON TRANSPORT; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; SYNTHESIS;

EID: 10844245455     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400289     Document Type: Article

References (45)

1. [1a] R. E. Del Sesto, A. M. Arif, J. J. Novoa, I. Anusiewicz, P. Skurski, J. Simons, B. C. Dunn, E. M. Eyring, J. S. Miller, J. Org. Chem. 2003, 68, 3367-3379.
2. [1b] D. V. Konarev, G. Zerza, M. Scharber, N. S. Sariciftci, R. N. Lyubovskaya, Synth. Met. 2001, 121, 1127-1128.
3. [1c] G. Chen, J. T. Lean, M. Alcala, T. E. Mallouk, J. Org. Chem. 2001, 66, 3027-3034.
4. [1d] D. V. Konarev, R. N. Lyubovskaya, N. V. Drichko, V. N. Semkin, A. Graja, Chem. Phys. Lett. 1999, 314, 570-576.
5. [1e] M. Ichida, T. Sohda, A. Nakamura, Chem. Phys. Lett. 1999, 310, 373-378.
6. [1f] V. A. Nadtochenko, A. A. Moravskii, V. V. Gritsenko, G. V. Shilov, O. A. Dyachenko, Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. C: Mol. Mater. 1996, 7, 103-104.
7. [1g] T. Dahl, Acta Chem. Scand. 1989, 43, 172-176.
8. [1h] Y. Yamaguchi, T. Nogami, H. Mikawa, I. Kumadaki, Y. Kobayashi, Bull. Chem. Soc. Jpn. 1983, 56, 1907-1911.
9. [2a] J. W. Sibert, P. B. Forshee, Inorg. Chem. 2002, 41, 5928-5930.
10. [2b] J. J. Wolff, A. Zietsch, B. Nuber, F. Gredel, B. Speiser, M. Würde, J. Org. Chem. 2001, 66, 2769-2777.
11. [2c] A. Ito, A. Taniguchi, T. Yamabe, K. Tanaka, Org. Lett. 1999, 741-743.
12. [2d] B. Speiser, M. Würde, C. Maichle-Mössmer, Chem. Eur. J. 1998, 4, 222-233.
13. [2e] T. Barth, C. Krieger, F. A. Neugebauer, H. A. Staab, Angew. Chem. Int. Ed. Engl. 1991, 30, 1028-1030.
14. [2f] D. A. Dixon, J. C. Calabrese, R. L. Harlow, J. S. Miller, Angew. Chem. Int. Ed. Engl. 1989, 28, 92-93.
15. [2g] K. Elbl-Weiser, C. Krieger, H. A. Staab, Angew. Chem. Int. Ed. Engl. 1990, 29, 211-213.
16. [2h] J. S. Miller, D. A. Dixon, J. C. Calabrese, C. Vazquez, P. J. Krusic, M. D. Ward, E. Wasserman, R. L. Harlow, J. Am. Chem. Soc. 1990, 112, 381-398.
17. [2i] K. Elbl-Weiser, F. A. Neugebauer, H. A. Staab, Tetrahedron Lett. 1989, 30, 6161-6164.
18. [2j] D. A. Dixon, J. C. Calabrese, R. L. Harlow, J. S. Miller, Angew. Chem. Int. Ed. Engl. 1989, 28, 92-94.
19. [2k] K. Elbl, C. Krieger, H. A. Staab, Angew. Chem. Int. Ed. Engl. 1986, 25, 1023-1024.
20. [3a] H. Takemura, H. Nakamichi, R. Nogita, T. Iwanaga, M. Yasutake, T. Shinmyozu, Tetrahedron Lett. 2003, 44, 5087-5089.
21. [3b] H. Takemura, N. Kon, M. Yasutake, T. Shinmyozu, Tetrahedron 2003, 59, 427-431.
22. [3c] H. Takemura, J. Inclusion Phenom. 2002, 42, 169-186.
23. [3d] H. Takemura, Recent Res. Dev. Org. Chem. 2000, 4, 201-225
24. [3e] H. Takemura, S. Nakashima, N. Kon, M. Yasutake, T. Shinmyozu, T. Inazu, J. Am. Chem. Soc. 2001, 123, 9293-9298.
25. [3f] N. Kon, H. Takemura, K. Otsuka, K. Tanoue, S. Nakashima, M. Yasutake, K. Tani, J. Kimoto, T. Shinmyozu, T. Inazu, J. Org. Chem. 2000, 65, 3708-3715.
26. [3g] H. Takemura, H. Kariyazono, N. Kon, T. Shinmyozu, T. Inazu, J. Org. Chem. 1999, 64, 9077-9079.
27. [3h] H. Takemura, K. Otsuka, N. Kon, M. Yasutake, T. Shinmyozu, T. Inazu, Tetrahedron Lett. 1999, 40, 5561-5564.
28. [3i] H. Takemura, T. Inazu, J. Synth. Org. Chem. Jpn. 1998, 56, 604-614.
29. [3j] H. Takemura, N. Kon, K. Tani, K. Takehara, J. Kimoto, T. Shinmyozu, T. Inazu, J. Chem. Soc., Perkin Trans. 1 1997, 239-246.
30. [3k] H. Takemura, T. Shinmyozu, T. Inazu, Coord. Chem. Rev. 1996, 156, 183-200.
31. [3l] G. Lee, M. Oka, H. Takemura, Y. Miyahara, N. Shimizu, T. Inazu, J. Org. Chem. 1996, 61, 8304-8306.
32. [3m] H. Takemura, S. Osada, T. Shinmyozu, T. Inazu, J. Chem. Soc., Perkin Trans. 1 1996, 277-280.
33. [3n] G. Wen, M. Matsunaga, T. Matsunaga, H. Takemura, T. Shinmyozu, Synlett 1995, 947-948.
34. [3o] T. Shinmyozu, N. Shibakawa, K. Sugimoto, H. Sakane, H. Takemura, K. Sako, T. Inazu, Synthesis 1993, 1257-1260.
35. F. Vögtle, Cyclophan-Chemie, Teubner, Stuttgart, 1990, pp. 184-193.
36. H. A. Staab, G. Gabel, C. Krieger, Chem. Ber. 1987, 120, 269-273.
37. H. Stetter, E.-E. Roos, Chem. Ber. 1954, 87, 566-571.
38. A. G. Giumanini, G. Chiavari, M. M. Musiani, P. Rossi, Synthesis 1980, 743-746.
39. 6, but with this reagent, 1c also decomposed before suitable crystals could grow.
40. M. Mascal, J.-L. Kerdelhué, A. S. Batsanov, M. J. Begley, J. Chem. Soc., Perkin Trans. 1 1996, 1141-1151.
41. [10a] H. Goto, E. Osawa, J. Am. Chem. Soc. 1989, 111, 8950-8951.
42. [10b] H. Goto, E. Osawa, J. Chem. Soc., Perkin Trans. 2 1993, 187-198.
43. A. R. Wartini, J. Valenzuela, H. A. Staab, F. A. Neugebauer, Eur. J. Org. Chem. 1998, 139-148.
44. [12a] A. Ito, A. Taniguchi, T. Yamabe, K. Tanaka, Org. Lett. 1999, 1, 741-743 and references therein.
45. [12b] T. Yao, S. Musha, M. Munemori, Chem. Lett. 1974, 939-944.