A highly stable double helix of aromatic oligoamide comprised of fused ring aromatic units

Tetrahedron

Volumn 68, Issue 23, 2012, Pages 4479-4484

  Gan, Quan ^a,c   Shang, Jie ^a,c   Kauffmann, Brice ^b   Wang, Ying ^a,c   Bie, Fusheng ^a,c   Jiang, Hua ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITÉ DE BORDEAUX   (France)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Double helices; Foldamers; Hybridization; Hydrogen bonds

Indexed keywords

AMIDE; AROMATIC COMPOUND; AROMATIC OLIGOAMIDE; BENZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 84860687367     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.081     Document Type: Article

References (52)

1. S. Hecht, and I. Huc Foldamers: Structure, Properties, and Applications 2007 Wiley-VCH Weinheim, Germany
2. G. Guichard, and I. Huc Chem. Commun. 2011 5933
3. I. Huc, and H. Jiang Organic Foldamers and Helices P.A. Gale, J.W. Steed, Supramolecular Chemistry: From Molecules to Nanomaterials 2011 Wiley Chichester, UK
4. D. Haldar, and C. Schmuck Chem. Soc. Rev. 38 2009 363
5. Q. Gan, Y. Wang, and H. Jiang Curr. Org. Chem. 15 2011 1293
6. B. Hasenknopf, J.-M. Lehn, G. Baum, and D. Fenske Proc. Natl. Acad. Sci. U.S.A. 93 1996 1397
7. C.R. Woods, M. Benaglia, F. Cozzi, and J.S. Siegel Angew. Chem., Int. Ed. 35 1996 1830
8. A. Orita, T. Nakano, D.L. An, K. Tanikawa, K. Wakamatsu, and J. Otera J. Am. Chem. Soc. 126 2004 10389
9. H. Katagiri, T. Miyagawa, Y. Furusho, and E. Yashima Angew. Chem., Int. Ed. 45 2006 1741
10. A. Marquis, V. Smith, J. Harrowfield, J.-M. Lehn, H. Herschbach, R. Sanvito, E. Leise-Wagner, and A.V. Dorsselaer Chem. - Eur. J. 12 2006 5632
11. S.H. Gellman Acc. Chem. Res. 31 1998 173
12. D.J. Hill, M.J. Mio, R.B. Prince, T.S. Hughes, and J.S. Moore Chem. Rev. 101 2001 3893
13. I. Huc Eur. J. Org. Chem. 1 2004 17
14. C.M. Goodman, S. Choi, S. Shandler, and W.F. DeGrado Nat. Chem. Biol. 3 2007 252
15. B. Gong Acc. Chem. Res. 41 2008 1376
16. I. Saraogi, and A.D. Hamilton Chem. Soc. Rev. 38 2009 1726
17. X. Zhao, and Z.T. Li Chem. Commun. 2010 1601
18. V. Berl, I. Huc, R. Khoury, M.J. Krische, and J.-M. Lehn Nature 407 2000 720
19. V. Berl, I. Huc, R. Khoury, and J.-M. Lehn Chem. - Eur. J. 7 2001 2810
20. C. Dolain, C. Zhan, J.-M. Léger, and I. Huc J. Am. Chem. Soc. 127 2005 2400
21. C. Zhan, J.-M. Léger, and I. Huc Angew. Chem., Int. Ed. 45 2006 4625
22. D. Haldar, H. Jiang, J.-M. Léger, and I. Huc Angew. Chem., Int. Ed. 45 2006 5483
23. E. Berni, B. Kauffmann, C. Bao, J. Lefeuvre, D. Bassani, and I. Huc Chem. - Eur. J. 13 2007 8463
24. E. Berni, J. Garric, C. Lamit, B. Kauffmann, J.-M. Léger, and I. Huc Chem. Commun. 2008 1968
25. D. Haldar, H. Jiang, J.-M. Léger, and I. Huc Tetrahedron 63 2007 6322
26. B. Baptiste, J. Zhu, D. Haldar, B. Kauffmann, J.-M. Léger, and I. Huc Chem. - Asian J. 5 2010 1364
27. Y. Ferrand, A.M. Kendhale, B. Kauffmann, A. Grélard, C. Marie, V. Blot, M. Pipelier, D. Dubreuil, and I. Huc J. Am. Chem. Soc. 132 2010 7858
28. Q. Gan, C. Bao, B. Kauffmann, A. Grélard, J. Xiang, S. Liu, I. Huc, and H. Jiang Angew. Chem., Int. Ed. 47 2008 1715
29. Q. Gan, F. Li, G. Li, B. Kauffmann, J. Xiang, I. Huc, and H. Jiang Chem. Commun. 2010 297
30. H. Goto, H. Katagiri, Y. Furusho, and E. Yashima J. Am. Chem. Soc. 128 2006 7176
31. H. Goto, Y. Furusho, and E. Yashima J. Am. Chem. Soc. 129 2007 109
32. H. Goto, Y. Furusho, and E. Yashima J. Am. Chem. Soc. 129 2007 9168
33. H. Goto, Y. Furusho, K. Miwa, and E. Yashima J. Am. Chem. Soc. 131 2009 471
34. H. Sugiura, Y. Nigorikawa, Y. Saiki, K. Nakamura, and M. Yamaguchi J. Am. Chem. Soc. 126 2004 14858
35. H. Sugiura, and M. Yamaguchi Chem. Lett. 36 2007 58
36. H. Sugiura, R. Amemiya, and M. Yamaguchi Chem. - Asian J. 3 2008 244
37. R. Amemiya, N. Saito, and M. Yamaguchi J. Org. Chem. 73 2008 7137
38. N. Saito, R. Terakawa, M. Shigeno, R. Amemiya, and M. Yamaguchi J. Org. Chem. 76 2011 4841
39. K. Yamamoto, H. Sugiura, R. Amemiya, H. Aikawa, Z. An, M. Yamaguchi, M. Mizukami, and K. Kurihara Tetrahedron 67 2011 5972
40. Y. Tanaka, H. Katagiri, Y. Furusho, and E. Yashima Angew. Chem., Int. Ed. 44 2005 3867
41. H. Ito, Y. Furusho, T. Hasegawa, and E. Yashima J. Am. Chem. Soc. 130 2008 14008
42. T. Maeda, Y. Furusho, S.-I. Sakurai, J. Kumaki, K. Okoshi, and E. Yashima J. Am. Chem. Soc. 130 2008 7938
43. J. Li, J.A. Wisner, and M.C. Jennings Org. Lett. 9 2007 3267
44. H.-B. Wang, B.P. Mudraboyina, J. Li, and M.C. Jennings Chem. Commun. 2010 7343
45. A. Acocella, A. Venturini, and F.J. Zerbetto J. Am. Chem. Soc. 126 2004 2362
46. B. Zhang, T. Yuan, H. Jiang, and M. Lei J. Phys. Chem. B 113 2009 10934
47. Z.-Q. Hu, H.-Y. Hu, and C.-F. Chen J. Org. Chem. 71 2006 1131
48. C. Bao, B. Kauffmann, Q. Gan, K. Srinivas, H. Jiang, and I. Huc Angew. Chem., Int. Ed. 47 2008 4153
49. M. Hudlicky, and H.M. Bell J. Fluorine Chem. 4 1974 19
50. © 1997-2002.
51. G.M. Sheldrick Acta Crystallogr., Sect. A 64 2008 112
52. L.J. Farrugia J. Appl. Crystallogr. 32 1999 837