Hydrogen Bond-Induced Rigid Oligoanthranilamide Ribbons That Are Planar and Straight

Organic Letters

Volumn 6, Issue 2, 2004, Pages 229-232

  Wu, Zong Quan ^a   Jiang, Xi Kui ^a   Zhu, Shi Zheng ^a   Li, Zhan Ting ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOBENZAMIDE; HYDROGEN; OLIGOMER; PHENYLENEDIAMINE DERIVATIVE; PHTHALIC ACID DERIVATIVE;

ARTICLE; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULE; PROTON NUCLEAR MAGNETIC RESONANCE; RIGIDITY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0842328410     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036108b     Document Type: Article

References (39)

1. Martin, R. E.; Diederich, F. Angew. Chem., Int. Ed. 1999, 38, 1350.
2. (b) Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
3. (c) Bunz, U. H. F. Acc. Chem. Res. 2001, 34, 998.
4. (a) Fyfe, M. C. T.; Stoddart, J. F. Acc. Chem. Res. 1997, 30, 393.
5. (b) Fujita, M. Chem. Soc. Rev. 1998, 27, 417.
6. (c) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853.
7. (d) Dinolfo, P. H.; Hupp, J. T. Chem. Mater. 2001, 13, 3113.
8. Okuyama, K.; Hasegawa, T.; Ito, M.; Mikami, N. J. Phys. Chem. 1984, 88, 1711.
9. (a) Bassani, D. M.; Lehn, J.-M.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 1845.
10. (b) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
11. (c) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
12. (d) Nowick, J. S. Acc. Chem. Res. 1999, 32, 287.
13. (e) Cheng, R. P.; Gellman, S. H.; Degrado, W. F. Chem. Rev. 2001, 101, 3219.
14. (f) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
15. (g) Cubberley, M. S.; Iverson, B. L. Curr. Opin. Chem. Biol. 2001, 5, 650.
16. (h) Sanford, A. R.; Gong, B. Curr. Org. Chem. 2003, 7, 1649.
17. (i) Zhao, D.; Moore, J. S. Chem. Commun. 2003, 807.
18. For recent examples of intramolecular hydrogen bonds for stablizing the planarity of π-conjugated folded systems, see: (a) Cary, J. M.; Moore, J. S. Org. Lett. 2002, 4, 4663. (b) Yang, X.; Brown, A. M.; Furukawa, M.; Li, S.; Gardinier, W. E.; Bukowski, E. J.; Bright, F. V.; Zheng, C.; Zeng, X. C.; Gong, B. Chem. Commun. 2003, 56. (c) Ernst, J. T.; Becceril, J.; Park, H. S.; Yin, H. ; Hamilton, A. D. Angew. Chem., Int. Ed. 2003, 43, 535.
19. For recent examples of intramolecular hydrogen bonds for stablizing the planarity of π-conjugated folded systems, see: (a) Cary, J. M.; Moore, J. S. Org. Lett. 2002, 4, 4663. (b) Yang, X.; Brown, A. M.; Furukawa, M.; Li, S.; Gardinier, W. E.; Bukowski, E. J.; Bright, F. V.; Zheng, C.; Zeng, X. C.; Gong, B. Chem. Commun. 2003, 56. (c) Ernst, J. T.; Becceril, J.; Park, H. S.; Yin, H. ; Hamilton, A. D. Angew. Chem., Int. Ed. 2003, 43, 535.
20. For recent examples of intramolecular hydrogen bonds for stablizing the planarity of π-conjugated folded systems, see: (a) Cary, J. M.; Moore, J. S. Org. Lett. 2002, 4, 4663. (b) Yang, X.; Brown, A. M.; Furukawa, M.; Li, S.; Gardinier, W. E.; Bukowski, E. J.; Bright, F. V.; Zheng, C.; Zeng, X. C.; Gong, B. Chem. Commun. 2003, 56. (c) Ernst, J. T.; Becceril, J.; Park, H. S.; Yin, H. ; Hamilton, A. D. Angew. Chem., Int. Ed. 2003, 43, 535.
21. For three-center hydrogen bonding in folding molecules, see: (a) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529. (b) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587. (c) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem. Eur. J. 2001, 7, 4352. (d) Gong, B.; Zeng, H.; Zhu, J.; Yuan, L.; Han, Y.; Cheng, S.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583.
22. For three-center hydrogen bonding in folding molecules, see: (a) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529. (b) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587. (c) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem. Eur. J. 2001, 7, 4352. (d) Gong, B.; Zeng, H.; Zhu, J.; Yuan, L.; Han, Y.; Cheng, S.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583.
23. For three-center hydrogen bonding in folding molecules, see: (a) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529. (b) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587. (c) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem. Eur. J. 2001, 7, 4352. (d) Gong, B.; Zeng, H.; Zhu, J.; Yuan, L.; Han, Y.; Cheng, S.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583.
24. For three-center hydrogen bonding in folding molecules, see: (a) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1996, 118, 7529. (b) Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587. (c) Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem. Eur. J. 2001, 7, 4352. (d) Gong, B.; Zeng, H.; Zhu, J.; Yuan, L.; Han, Y.; Cheng, S.; Furukawa, M.; Parra, R. D.; Kovalevsky, A. Y.; Mills, J. L.; Skrzypczak-Jankun, E.; Martinovic, S.; Smith, R. D.; Zheng, C.; Szyperski, T.; Zeng, X. C. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11583.
25. For an example of hydrogen-bond-mediated polyarenes, see: Delnoye, D. A. P.; Sijbesma, R. P.; Vekemans, J. A. J. M.; Meijer, E. W. J. Am. Chem. Soc. 1996, 118, 8717.
26. For reviews of covalent bond-mediated molecular ribbons, see: (a) Kohnke, F. H.; Stoddart, J. F. Pure Appl. Chem. 1989, 61, 1581. (b) Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119. (c) Schröder, A.; Mekelburger, H.-B.; Vögtle, F. Top. Curr. Chem. 1994, 172, 179.
27. For reviews of covalent bond-mediated molecular ribbons, see: (a) Kohnke, F. H.; Stoddart, J. F. Pure Appl. Chem. 1989, 61, 1581. (b) Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119. (c) Schröder, A.; Mekelburger, H.-B.; Vögtle, F. Top. Curr. Chem. 1994, 172, 179.
28. For reviews of covalent bond-mediated molecular ribbons, see: (a) Kohnke, F. H.; Stoddart, J. F. Pure Appl. Chem. 1989, 61, 1581. (b) Girreser, U.; Giuffrida, D.; Kohnke, F. H.; Mathias, J. P.; Philp, D.; Stoddart, J. F. Pure Appl. Chem. 1993, 65, 119. (c) Schröder, A.; Mekelburger, H.-B.; Vögtle, F. Top. Curr. Chem. 1994, 172, 179.
29. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
30. Sinnreich, J. Synthesis 1980, 578.
31. Marvel, K. J. Org. Chem. 1953, 18, 707.
32. Itami, K.; Palmgren, A.; Thorarensen, A.; Bäckvall, J.-E. J. Org. Chem. 1998, 63, 6466.
33. Kesseler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512.
34. (a) Shetty, A. S.; Zhang, J. S.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019.
35. (b) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651.
36. (c) Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagano, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350.
37. (a) Legon, A. C. Chem. Soc. Rev. 1990, 19, 197.
38. (b) Nowick, J. S.; Powell, N. A.; Martinez, E. J.; Smith, E. M.; Noronha, G. J. Org. Chem. 1992, 57, 3763.
39. (c) Dado, G. P.; Gellman, S. H. J. Am. Chem. Soc. 1994, 116, 1054.