One-pot synthesis of permethylated α-CD-based rotaxanes having alkylene chain axles and their structural characteristics

Chemistry Letters

Volumn 41, Issue 8, 2012, Pages 806-808

  Akae, Yosuke ^a   Arai, Takayuki ^a,b   Koyama, Yasuhito ^a   Okamura, Hisashi ^a   Johmoto, Kohei ^a   Uekusa, Hidehiro ^a   Kuwata, Shigeki ^a   Takata, Toshikazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b LINTEC CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84864479947     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2012.806     Document Type: Article

References (64)

1. (a) A. Harada, J. Li, M. Kamachi, Nature 1992, 356, 325.
2. (b) A. Harada, J. Li, M. Kamachi, Nature 1994, 370, 126.
3. For selected reviews, see: a) H. W. Gibson, M. C. Bheda, P. T. Engen, Prog. Polym. Sci. 1994, 19, 843.
4. (b) S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959.
5. c) Molecular Catenanes, Rotaxanes and Knots: A Journey Through the World of Molecular Topology, ed. by J.-P. Sauvage, C. Dietrich-Buchecker, WileyVCH, New York, Weinheim, 1999.
6. (d) A.Harada, Acta Polym. 1998, 49, 3.
7. (e) A. Harada, Acc. Chem. Res. 2001, 34, 456.
8. (f) T. Takata, N. Kihara, Y. Furusho, Adv. Polym. Sci. 2004, 171, 1.
9. (g) T. Takata, Polym. J. 2006, 38, 1.
10. (h) M. J. Frampton, H. L. Anderson, Angew. Chem., Int. Ed. 2007, 46, 1028.
11. (i) K. Ito, Polym. J. 2007, 39, 489.
12. (j) J. Araki, K. Ito, Soft Matter 2007, 3, 1456.
13. (k) J. Li, X. J. Loh, Adv. Drug Delivery Rev. 2008, 60, 1000.
14. (l) N. Yui, R. Katoono, A. Yamashita, Adv. Polym. Sci. 2009, 222, 55.
15. (m) A. Harada, A. Hashidzume, H. Yamaguchi, Y. Takashima, Chem. Rev. 2009, 109, 5974.
16. (n) A. Harada, Y. Takashima, H. Yamaguchi, Chem. Soc. Rev. 2009, 38, 875.
17. (o) F. van de Manakker, T. Vermonden, C. F. van Nostrum, W. E. Hennink, Biomacromolecules 2009, 10, 3157.
18. (p) Supramolecular Polymer Chemistry, ed. by A. Harada, Wiley-VCH, Weinheim, 2012.
19. For related reports concerning synthesis of CD-containing polyrotaxane, see: a) G. Wenz, B. Keller, Angew. Chem., Int. Ed. Engl. 1992, 31, 197.
20. (b) W. Herrmann, M. Schneider, G. Wenz, Angew. Chem., Int. Ed. Engl. 1997, 36, 2511.
21. (c) T. Zhao, H. W. Beckham, Macromolecules 2003, 36, 9859.
22. (d) M. Okada, Y. Takashima, A. Harada, Macromolecules 2004, 37, 7075.
23. (e) J. Araki, C. Zhao, K. Ito, Macromolecules 2005, 38, 7524.
24. (f) G. Fleury, C. Brochon, G. Schlatter, G. Bonnet, A. Lapp, G. Hadziioannou, Soft Matter. 2005, 1, 378.
25. (g) T. Ooya, H. Utsunomiya, M. Eguchi, N. Yui, Bioconjugate Chem. 2005, 16, 62.
26. (h) S. Loethen, T. Ooya, H. S. Choi, N. Yui, D. H. Thompson, Biomacromolecules 2006, 7, 2501.
27. (i) G. Wenz, B.-H. Han, A. Müller, Chem. Rev. 2006, 106, 782.
28. (j) S. Loethen, J.-M. Kim, D. H. Thompson, Pol. Rev. 2007, 47, 383.
29. (k) K. Kato, H. Komatsu, K. Ito, Macromolecules 2010, 43, 8799.
30. (a) T. Ooya, N. Yui, Macromol. Chem. Phys. 1998, 199, 2311.
31. (b) H. Fujita, T. Ooya, N. Yui, Polym. J. 1999, 31, 1099.
32. (c) H. Fujita, T. Ooya, N. Yui, Macromolecules 1999, 32, 2534.
33. (d) H. Fujita, T. Ooya, N. Yui, Macromol. Chem. Phys. 1999, 200, 706.
34. (e) T. Ikeda, T. Ooya, N. Yui, Polym. J. 1999, 31, 658.
35. (f) H. S. Choi, K. M. Huh, T. Ooya, N. Yui, J. Am. Chem. Soc. 2003, 125, 6350.
36. (g) T. Ooya, M. Eguchi, N. Yui, J. Am. Chem. Soc. 2003, 125, 13016.
37. (h) Y. Tachibana, N. Kihara, Y. Furusho, T. Takata, Org. Lett. 2004, 6, 4507.
38. (i) H. Hirose, H. Sano, G. Mizutani, M. Eguchi, T. Ooya, N. Yui, Polym. J. 2006, 38, 1093.
39. (j) Y. Makita, N. Kihara, T. Takata, J. Org. Chem. 2008, 73, 9245.
40. (k) K. Nakazono, K. Fukasawa, T. Sato, Y. Koyama, T. Takata, Polym. J. 2010, 42, 208.
41. (l) F. Ishiwari, K.-i. Fukasawa, T. Sato, K. Nakazono, Y. Koyama, T. Takata, Chem.®Eur. J. 2011, 17, 12067
42. (m) F. Ishiwari, K. Nakazono, Y. Koyama, T. Takata, Chem. Commun. 2011, 47, 11739.
43. (n) Y. Kohsaka, Y. Koyama, T. Takata, Angew. Chem., Int. Ed. 2011, 50, 10417.
44. a) K.-i. Yoshida, T. Shimomura, K. Ito, R. Hayakawa, Langmuir 1999, 15, 910.
45. (b) T. Shimomura, K.-i. Yoshida, K. Ito, R. Hayakawa, Polym. Adv. Technol. 2000, 11, 837.
46. (c) I. Yamaguchi, I. Nurulla, T. Yamamoto, Kobunshi Ronbunshu 2000, 57, 472.
47. (d) P. N. Taylor, M. J. O'Connell, L. A. McNeill, M. J. Hall, R. T. Aplin, H. L. Anderson, Angew. Chem., Int. Ed. 2000, 39, 3456.
48. (e) M. J. Frampton, H. L. Anderson, Angew. Chem., Int. Ed. 2007, 46, 1028.
49. (f) J. Terao, S. Tsuda, Y. Tanaka, K. Okoshi, T. Fujihara, Y. Tsuji, N. Kambe, J. Am. Chem. Soc. 2009, 131, 16004.
50. a) Y. Okumura K. Ito Adv. Mater 2001 13 485.
51. (b) T. Karino, Y. Okumura, K. Ito, M. Shibayama, Macromolecules 2004, 37, 6177.
52. (c) T. Oku, Y. Furusho, T. Takata, Angew. Chem., Int. Ed. 2004, 43, 966.
53. (d) T. Bilig, T. Oku, Y. Furusho, Y. Koyama, S. Asai, T. Takata, Macromolecules 2008, 41, 8496.
54. (e) Y. Kohsaka, K. Nakazono, Y. Koyama, S. Asai, T. Takata, Angew. Chem., Int. Ed. 2011, 50, 4872.
55. (f) M. Ogawa, A. Kawasaki, Y. Koyama, T. Takata, Polym. J. 2011, 43, 909.
56. K.Miyake, S. Yasuda, A. Harada, J. Sumaoka, M. Komiyama, H. Shigekawa, J. Am. Chem. Soc. 2003, 125, 5080.
57. a)M. Noltemeyer, W. Saenger, Nature 1976, 259, 629.
58. (b) K. Harata, F. Hirayama, K. Uekama, G. Tsoucaris, Chem. Lett. 1988, 1585.
59. a) T. Arai T. Takata Chem. Lett 2007 36 418.
60. (b) T. Arai, M. Hayashi, N. Takagi, T. Takata, Macromolecules 2009, 42, 1881.
61. (c) K. Nakazono, T. Takashima, T. Arai, Y. Koyama, T. Takata, Macromolecules 2010, 43, 691.
62. Y. Akae, H. Okamura, Y. Koyama, T. Arai, T. Takata, Org. Lett. 2012, 14, 2226.
63. Crystallographic data of 3: C138H238N4O62, Mr = 2945.32, I4122 (#98), a = 17.9461(3) Å, c = 55.1640(10)Å, V = 17766.3(5)i3, Z = 4, Dcalcd = 1.101Mgm13, All 8154 unique reflections (Rint = 0.0417) were used for refinement, Final R indices R1 = 0.0765 (I> 2 (I )) and wR2 = 0.2712 for all data. Details are deposited as a part of ESI. Crystallographic data reported in this manuscript have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-876327. Copies of the data can be obtained free of charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, U.K.; fax: +44 1223 336033; or deposit@ccdc.cam.ac.uk).
64. Supporting Information is also available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index. html.