Shape-persistent aromatic amide oligomers: New tools for supramolecular chemistry

Chemistry - An Asian Journal

Volumn 1, Issue 6, 2006, Pages 766-778

  Li, Zhan Ting ^a   Hou, Jun Li ^a   Li, Chuang ^a   Yi, Hui Ping ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Amides; Foldamers; Hydrogen bonds; Molecular recognition; Self assembly

Indexed keywords

AMIDE; MACROCYCLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON;

CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; METHODOLOGY; ORGANIC CHEMISTRY; REVIEW; SYNTHESIS;

AMIDES; CHEMISTRY, ORGANIC; HYDROGEN BONDING; MACROCYCLIC COMPOUNDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC;

EID: 33845985639     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600186     Document Type: Review

References (75)

1. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173.
2. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893.
3. M. S. Cubberley, B. L. Iverson, Curr. Opin. Chem. Biol. 2001, 5, 650.
4. C. Schmuck, Angew. Chem. 2003, 115, 2552;
5. Angew. Chem. Int. Ed. 2003, 42, 2448.
6. I. Huc, Eur. J. Org. Chem. 2004, 17.
7. a) B. Gong, Chem. Eur. J. 2001, 7, 4337;
8. b) A. Sanford, K. Yamato, X. W. Yang, L. H. Yuan, Y. H. Han, B. Gong, Eur. J. Biochem. 2004, 271, 1416.
9. R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219.
10. a) J. T. Ernst, J. Becerril, H. S. Park, H. Yin, A. D. Hamilton, Angew. Chem. 2003, 115, 553;
11. Angew. Chem. Int. Ed. 2003, 42, 535;
12. b) H. Yin, A. D. Hamilton, Angew. Chem. 2005, 117, 4200;
13. Angew. Chem. Int. Ed. 2005, 44, 4130.
14. a) Y. Hamuro, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1996, 118, 7529;
15. b) Y. Hamuro, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1997, 119, 10587.
16. a) R. D. Parra, H. Q. Zeng, J. Zhu, C. Zheng, X. C. Zeng, B. Gong, Chem. Eur. J. 2001, 7, 4352;
17. b) B. Gong, H. Zeng, J. Zhu, L. Yuan, Y. Han, S. Cheng, M. Furukawa, R. D. Parra, A. Y. Kovalevsky, J. L. Mills, E. Skrzypczak-Jankun, S. Martinovic, R. D. Smith, C. Zheng, T. Szyperski, X. C. Zeng, Proc. Natl. Acad. Sci. USA 2002, 99, 11583;
18. c) A. Sanford, B. Gong, Curr. Org. Chem. 2003, 7, 1649;
19. d) L. Yuan, H. Q. Zeng, K. Yamato, A. R. Sanford, W. Feng, H. Atreya, D. K. Sukumaran, T. Szyperski, B. Gong, J. Am. Chem. Soc. 2004, 126, 16528.
20. a) H. Jiang, J.-M. Léger, I. Hue, J. Am. Chem. Soc. 2003, 125, 3448;
21. b) H. Jiang, J.-M. Leger, C. Dolain, P. Guionneau, I. Huc, Tetrahedron 2003, 59, 8365;
22. c) H. Jiang, C. Dolain, J.-M. Leger, H. Gornitzka, I. Hue, J. Am. Chem. Soc. 2004, 126, 1034;
23. d) V. Maurizot, C. Dolain, Y. Leydet, J.-M. Leger, P. Guionneau, I. Hue, J. Am. Chem. Soc. 2004, 126, 10049.
24. D. Kanamori, T. Okamura, H. Yamamoto, N. Ueyama, Angew. Chem. 2005, 117, 991;
25. Angew. Chem. Int. Ed. 2005, 44, 969.
26. a) H. A. K. Howard, V. J. Hoy, D. O'Hagan, G. T. Smith, Tetrahedron 1996, 52, 12613;
27. b) J. D. Dunitz, R. Taylor, Chem. Eur. J. 1997, 3, 89;
28. c) J. D. Dunitz, ChemBioChem 2004, 5, 614.
29. a) X. Zhao, X.-Z. Wang, X.-K. Jiang, Y.-Q. Chen, Z.-T. Li, G.-J. Chen, J. Am. Chem. Soc. 2003, 125, 15128;
30. b) C. Li, S.-F. Ren, J.-L. Hou, H.-P. Yi, S.-Z. Zhu, X.-K. Jiang, Z.-T. Li, Angew. Chem. 2005, 117, 5871;
31. Angew. Chem. Int. Ed. 2005, 44, 5725.
32. For F⋯H-N bonds in aliphatic amides, see: F. Hof, D. M. Scofield, W. B. Schweizer, F. Diederich, Angew. Chem. 2004, 116, 5166;
33. Angew. Chem. Int. Ed. 2004, 43, 5056.
34. P. S. Corbin, S. C. Zimmerman, P. A. Thiessen, N. A. Hawryluk, T. J. Murray, J. Am. Chem. Soc. 2001, 123, 10475.
35. D. A. P. Delnoye, R. P. Sijbesma, J. A. Kekemans, E. W. Meijer, J. Am. Chem. Soc. 1996, 118, 8717.
36. Z.-Q. Wu, X.-K. Jiang, S.-Z. Zhu, Z.-T. Li, Org. Lett. 2004, 6, 229.
37. C. A. Hunter, A. Spitaleri, S. Toma, Chem. Commun. 2005, 3691.
38. Z.-Q. Hu, H.-Y. Hu, C.-F. Chen, J. Org. Chem. 2006, 71, 1131.
39. J. Zhu, X.-Z. Wang, X.-B. Shao, J.-L. Hou, X.-Z. Chen, X.-K. Jiang, Z.-T. Li, J. Org. Chem. 2004, 69, 6221.
40. B. Huang, M. A. Prantil, T. L. Gustafson, J. R. Parquette, J. Am. Chem. Soc. 2003, 125, 14518.
41. J. J. van Gorp, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2002, 124, 14759.
42. H. M. Keizer, R. P. Sijbesman, Chem. Soc. Rev. 2005, 34, 226.
43. L. Yuan, W. Feng, K. Yamato, A. R. Sanford, D. Xu. H. Guo, B. Gong, J. Am. Chem. Soc. 2004, 126, 11120.
44. Y. H. Kim, J. Calabrese, C. McEwen, J. Am. Chem. Soc. 1996, 118, 1545.
45. Y.-Q. Chen, X.-Z. Wang, X.-B. Shao, J.-L. Hou, X.-Z. Chen, X.-K. Jiang, Z.-T. Li, Tetrahedron 2004, 60, 10253.
46. Z.-Q. Wu, X.-K. Jiang, Z.-T. Li, Tetrahedron Lett. 2005, 46, 8067.
47. H. Jiang, J.-M. Léger, P. Guionneau, I. Huc, Org. Lett. 2004, 6, 2985.
48. A. Zhang, Y. Han, K. Yamato, X. C. Zheng, B. Gong. Org. Lett. 2006, 8, 803.
49. R. W. Sinkeldam, M. H. C. J. van Houtem, G. Koeckelberghs, J. A. J. M. Vekemans, E. W. Meijer, Org. Lett. 2006, 8, 383.
50. M. T. Stone, J. M. Heemstra, J. S. Moore, Acc. Chem. Res. 2006, 39, 11.
51. M. Inouye, M. Waki, H. Abe, J. Am. Chem. Soc. 2004, 126, 2022.
52. J.-L. Hou, M.-X. Jia, X.-K. Jiang, Z.-T. Li, G.-J. Chen. J. Org. Chem. 2004, 69, 6228.
53. K.-J. Chang, B.-N. Kang, M.-H. Lee, K.-S. Jeong, J. Am. Chem. Soc. 2005, 127, 12214.
54. J.-L. Hou, X.-B. Shao, G.-J. Chen, Y-X. Zhou, X.-K. Jiang, Z.-T. Li, J. Am. Chem. Soc. 2004, 126, 12386.
55. H.-P. Yi, X.-B. Shao, J.-L. Hou, C. Li, X.-K. Jiang, Z.-T. Li, New J. Chem. 2005, 29, 1213.
56. H.-P. Yi, C. Li, J.-Li Hou, X.-K. Jiang, Z.-T. Li, Tetrahedron 2005, 61, 7974.
57. P. R. Ashton, P. J. Campbell, E. J. T. Chrystal, P. T. Glink, P. S. Menzer, D. Philip, N. Spencer, J. F. Stoddart, P. A. Tasker. D. J. Williams, Angew. Chem. 1995, 107, 1907;
58. Angew. Chem. Int. Ed. Engl. 1995, 34, 1865.
59. a) S. C. Zimmerman, Top. Curr. Chem. 1993, 165, 71;
60. b) M. Harmata, Acc. Chem. Res. 2004, 37, 862.
61. Z.-Q. Wu, X.-B. Shao, C. Li, J.-L. Hou, K. Wang, X.-K. Jiang, Z.-T. Li, J. Am. Chem. Soc. 2005, 127, 17460.
62. For recent reviews on porphyrin-fullerene complexation, see: a) P. D. Boyd, C. A. Reed, Acc. Chem. Res. 2005, 38, 235;
63. b) A. Satake, Y. Kobuke, Tetrahedron 2005, 61, 13.
64. a value of the discrete zinc porphyrin units; see: W.-S. Li, D.-L. Jiang, Y. Suna, T. Aida, J. Am. Chem. Soc. 2005, 127, 7700.
65. R. Kessinger, C. Thilgen, T. Mordasini, F. Diederich, Helv. Chim. Acta 2000, 83, 3069.
66. J.-L. Hou, H.-P. Yi, X.-B. Shao, C. Li, Z.-Q. Wu, X.-K. Jiang, L.-Z. Wu, C.-H. Tung, Z.-T. Li, Angew. Chem. 2006, 118, 810;
67. Angew. Chem. Int. Ed. 2006, 45, 796.
68. I. Huc, V. Maurizot, H. Gornitzka, J.-M. Léger, Chem. Commun. 2002, 578.
69. J. Garric, J.-M. Léger, I. Huc, Angew. Chem. 2005, 117, 1990;
70. Angew. Chem. Int. Ed. 2005, 44, 1954.
71. For a recent review on molecular encapsulation, see: J. Rebek, Jr., Angew. Chem. 2005, 117, 2104;
72. Angew. Chem. Int. Ed. 2005, 44, 2068.
73. C. Dolain, C. Zhan, J.-M. Léger, L. Daniels, I. Huc, J. Am. Chem. Soc. 2005, 127, 2400.
74. M. C. Feiters in Supramolecular Technology, Comprehensive Supramolecular Chemistry, Vol. 10 (Ed.: D. N. Reinhoudt), Elsevier, Amsterdam, 1996, p. 267.
75. Although this review focuses on the applications of aromatic amide based folding and related secondary structures in supramolecular chemistry, studies by Hamilton and co-workers demonstrated their potential in chemical biology and related areas; see reference [8].