Synthesis and functionalization of 3,3′-bis(spirodienone)-bridged 2,2′-bithiophene: A new building block for redox-active molecular switching materials

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3837-3840

  Kurata, Hiroyuki ^a   Kim, Sang ^a   Fujimoto, Takahisa ^a   Matsumoto, Kouzou ^a   Kawase, Takeshi ^a,b   Kubo, Takashi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349112030     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8015379     Document Type: Article

References (46)

1. (a) Bäuerle, P. In Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1999; pp 89-182.
2. (b) Takimiya, K.; Kato, K.; Aso, Y.; Ogura, F.; Otsubo, T. Bull. Chem. Soc. Jpn. 2002, 75, 1795.
3. (c) Okamoto, T.; Kudoh, K.; Wakamiya, A.; Yamaguchi, S. Chem. Eur. J. 2006, 13, 548.
4. (d) Payne, M. M.; Odom, S. A.; Parkin, S. R.; Anthony, J. E. Org. Lett. 2004, 6, 3325.
5. (e) Pan, H.; Li, Y.; Wu, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. Chem. Mater. 2006, 18, 3237.
6. (f) Nicolas, Y.; Blanchard, P.; Levillain, E.; Magali Allain, M.; Nicolas Mercier, N.; Roncali, J. Org. Lett. 2004, 6, 273.
7. (g) Andrzej Rajca, A.; Rajca, S.; Pink, M.; Miyasaka, M. Synlett 2007, 1799, and references therein,
8. (h) Liu, W.-J.; Zhou, Y.; Ma, Y.; Cao, Y.; Wang, J.; Pei, J. Org. Lett. 2007, 9, 4187.
9. (a) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, 2001.
10. (b) Balzani, V.; Venturi, M.; Credi, A. Molecular Devices and Machines; Wiley-VCH: Weinheim, 2003.
11. (c) Feringa, B. L. J. Org. Chem. 2007, 72, 6635.
12. (a) Irie, M. Chem. Rev. 2000, 100, 1685.
13. (b) Matsuda, K.; Irie, M. Chem. Lett. 2006, 35, 1204.
14. (a) Sugiyasu, K.; Swager, T. M Bull. Chem. Soc. Jpn. 2007, 80, 2074. references therein,
15. (b) Nishida, J.; Miyagawa, T.; Yamashita, Y. Org. Lett. 2004, 6, 2523.
16. (e) Tanifuji, N.; Irie, M.; Matsuda, M. Chem. Lett. 2005, 34, 1580.
17. (a) Kurata, H.; Tanaka, T.; Oda, M. Chem. Lett. 1999, 749.
18. (b) Kurata, H.; Takehara, Y.; Kawase, T.; Oda, M. Chem. Lett. 2003, 32, 538.
19. (c) Kurata, H.; Takehara, Y.; Matsumoto, K.; Kawase, T.; Oda, M. Chem. Lett. 2005, 34, 1660.
20. (d) Kurata, H.; Takakuwa, H.; Imai, N.; Matsumoto, K.; Kawase, T.; Oda, M. Bull. Chem. Soc. Jpn. 2007, 80, 1402.
21. Kurata, H.; Kim, S.; Matsumoto, K.; Kawase, T.; Oda, M. Chem. Lett. 2007, 36, 386.
22. Helical conformations of 3,3′-diaryl-2,2′-bithiophenes have been reported. Almutairi, A.; Tham, F. S.; Marsella, M. J Tetrahedron 2004, 60, 7187.
23. (a) Chadwick, J. E.; Kohler, B. E. J. Phys. Chem. 1994, 98, 3631.
24. (b) Belletête, M.; Leclerc, M.; Durocher, G. J. Phys. Chem. 1994, 98, 9450.
25. (c) Wong, K-T.; Hung, T. H.; Kao, S. C.; Chou, C. H.; Su, Y. O. Chem. Commun. 2001, 1268.
26. (d) Marsella, M. J.; Rahbarnia, S.; Wilmot, N. Org. Biomoi Chem. 2007, 5, 391.
27. (e) Bouzzine, S. M.; Makayssi, A.; Hamidi, A. M.; Bouachrine, M. THEOCHEM 2008, 851, 254.
28. Yamamoto, T.; Hayashi, H. J. Poly. Sci. A 1997, 35, 463.
29. (a) Xie, C.; Lahti, P. M. J. Poly. Sci. A 1999, 37, 779.
30. (b) Miyasaka, M.; Yamazaki, T.; Tsuchida, E.; Nishide, H. Macromolecules 2000, 33, 8511.
31. (c) Xie, C.; Lahti, P. M.; George, C. Org. Lett. 2000, 2, 3417.
32. (d) Caironi, M.; Natali, D.; Sampietro, M.; Bertarelli, C.; Bianco, A.; Dundulachi, A.; Canesi, E.; Zerbi, G. Appl. Phys. Lett. 2006, 89, 246519.
33. Kurata, H.; Takehara, Y; Kim, S.; Sakai, K.; Matsumoto, K.; Kawase, T.; Oda, M Synlett 2007, 2053.
34. (a) Gronowitz, S. Acta Chem. Scand. 1961, 15, 1393.
35. (b) Dahlmann, U.; Neidlein, R. Helv. Chim. Acta 1996, 79, 755.
36. -1 (Mo Kα λ = 0.71070 Å), 16627 reflections measured, 16460 unique, reflection/parameter ratio = 20.60, R = 0.064 for I > 2σ(I), wR = 0.206 for all data. GOF = 0.83.
37. Recently, a trispiro-conjoined cyclopropane derivative having a similar bis(spirodienone) structure has been reported and the bond length of the two spiro-carbons was 1.595(8) Å. Kiyohara, S.; Ishizuka, K.; Wakabayashi, H.; Miyamae, H.; Kanazumi, M.; Kato, T.; Kobayashi, K Tetrahedron Lett. 2007, 48, 6877.
38. (a) Kirchbaum, T.; Azumi, R.; Mena-Osteritz, E.; Bäuerle, T P. New J. Chem. 1999, 241.
39. (b) Pei, J.; Ni, J.; Zhou, X.-H.; Cao, X.-Y.; Lai, Y.-H. J. Org. Chem. 2002, 67, 4924.
40. 4 (0.1 M) as the supporting electrolyte. Scan rate was 100 mV/s.
41. (a) Suzuki, T.; Ohta, E.; Kawai, H.; Fujiwara, K.; Fukushima, T Synlett 2007, 851, and references therein,
42. (b) Ohta, A.; Ueki, C.; Uchiyama, Y.; Fujimori, K. Heterocydes 2006, 69, 365.
43. (c) Bryce, M. R.; Coffin, M. A.; Hursthouse, M. B.; Karaulov, A. I.; Müllen, K.; Scheich, H. Tetrahedron Lett. 1991, 32, 6029.
44. (a) Suzuki, T.; Shiohara, H.; Monobe, M.; Sakimura, T.; Tanaka, S.; Yamashita, Y.; Miyashi, T. Angew. Chem., Int. Ed. Engl. 1992, 31, 455.
45. (b) Henderson, J. C.; Kiya, Y.; Hutchison, G. R.; Abrufta, H. D. J. Phys. Chem. C 2008, 112, 3989.
46. Hock, J.; Thompson, A. M; W, C.; McCleverty, J. A.; Ward, M. D. J. Chem. Soc., Dalton Trans. 1996, 4257.