First zipper-featured molecular duplexes driven by cooperative donor-acceptor interaction

Organic Letters

Volumn 5, Issue 11, 2003, Pages 1955-1958

  Zhou, Qi Zhong ^a   Jiang, Xi Kui ^a   Shao, Xue Bin ^a   Chen, Guang Ju ^b   Jia, Mu Xin ^b   Li, Zhan Ting ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b BEIJING NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIOXYBENZENE; 1,5 DIOXYNAPHTHALENE; BENZENE DERIVATIVE; IMIDE; NAPHTHALENE DERIVATIVE; PYROMELLITIC DIIMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON; MOLECULAR MODEL; OSMOSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY; VAPOR PRESSURE;

EID: 0141853006     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034549p     Document Type: Article

References (39)

1. Horton, R. H.; Moran, L. A.; Ochs, R. S.; Rawn, D. J.; Scrimgeour, G. K. Principles of Biochemistry; Prentice Hall Internaltional, Inc.: London, UK, 1992.
2. (a) Fatin-Rouge, N.; Blanc, S.; Pfeil, A.; Rigault, A.; Albrecht-Gary, A.-M.; Lehn, J.-M. Help. Chim. Acta 2001, 84, 1694.
3. (b) Berl, V.; Huc, I.; Khoury, R. G.; Lehn, J.-M. Chem. Eur. J. 2001, 7, 2810.
4. (a) Taylor, P. N.; Anderson, H. L. J. Am. Chem. Soc. 1999, 121, 11538.
5. (b) Anderson, H. L. Chem. Commun. 1999, 2323.
6. (a) Schmuck, C.; Heil, M. Org. Lett. 2001, 3, 1253.
7. (b) Sanchez-Quesada, J.; Seel, C.; Prados, P.; de Mendoza, J.; Dalcol, I.; Giralt, E. J. Am. Chem. Soc. 1996, 118, 277.
8. (a) Carver, F. J.; Hunter, C. A.; Jones, P. S.; Livingstone, D. J.; McCabe, J. F.; Seward, E. M.; Tiger, P.; Spey, S. E. Chem. Eur. J. 2001, 7, 4854.
9. (b) Bisson, A. P.; Carver, F. J.; Eggleston, D. S.; Haltimanger, R. C.; Hunter, C. A.; Livingstone, D. L.; McCabe, J. F.; Rotger, C.; Rowan, A. E. J. Am. Chem. Soc. 2000, 122, 8856.
10. (a) Corbin, P. S.; Zimmerman, S. C.; Thiessen, P. A.; Hawryluk, N. A.; Murray, T. J. J. Am. Chem. Soc. 2001, 123, 10475.
11. (b) Gong, B.; Yang, Y.; Zeng, H.; Skrzypczak-Jankunn, E.; Kim, Y. W.; Zhu, J.; Ickes, H. J. Am. Chem. Soc. 1999, 121, 5607.
12. (c) Beijer, F. H.; Sijbesma, R. P.; Kooijman, H.; Spek, A. L.; Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 6761.
13. (d) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726.
14. (a) Hamilton, D. G.; Lynch, D. E.; Byriel, K. A.; Kennard, C. H. L.; Sanders, J. K. M. Aust. J. Chem. 1998, 51, 441.
15. (b) Hamilton, D. G.; Lynch, D. E.; Byriel, K. A.; Kennard, C. H. L. Aust. J. Chem. 1997, 50, 439.
16. (c) Peover, M. E. Trans. Faraday Soc. 1962, 58, 2370.
17. (a) Hamilton, D. G.; Feeder, N.; Prodi, L.; Teat, S. J.; Clegg, W.; Sanders, J. K. M. J. Am. Chem. Soc. 1998, 120, 1096.
18. (b) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. Eur. J. 1998, 4, 608.
19. (c) Hamilton, D. G.; Sanders, J. K. M.; Davies, J. E.; Clegg, W.; Teat, S. J. Chem. Commun. 1997, 897.
20. (a) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154.
21. (b) Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.
22. (a) Nagata, T. Bull. Chem. Soc. Jpn. 1991, 64, 4; 3005.
23. (b) Hunter, C. A.; Sanders, J., K. M.; Beddard, G. S.; Evans, S. J. Chem. Soc., Chem. Commun. 1989, 1765.
24. (a) 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.
25. (b) Cubberley, M. S.; Iverson, B. L. J. Am. Chem. Soc. 2001, 123, 7560.
26. 1H NMR and one of them was used for titration analysis.
27. (a) Conners, K. A. Binding Constants: The Measurement of Molecular Complex Stability; Wiley: New York, 1987.
28. (b) Wilcox, C. S. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Dürr, H., Eds.; VCH: New York, 1991; p 123.
29. 3. Although an important change of the chemical shifts of the H-1 of 2 was also exhibited, no good results of association constants could be derived by fitting to a nonlinear binding equation appropriate for a 1:1 or 1:2 binding model, revealing that more complicated binding models might exist.
30. Job, P. Ann. Chim. Ser. 10 1928, 9, 113.
31. (a) Zych, A. J.; Iverson, B. L. J. Am. Chem. Soc., 2000, 122, 8898
32. (b) Hamilton, D. G.; Montalti, M.; Prodi, L.; Fontani, M.; Zanello, P.; Sanders, J. K. M. Chem. Eur. J. 2000, 6, 608.
33. (c) Lokey, R. S.; Iverson, B. L. J. Am. Chem. Soc. 1999, 121, 2639
34. Berdague, P.; Perez, F.; Courtieu, J.; Bayle, J. P. Bull. Soc. Chim. Fr. 1993, 130, 475.
35. (a) Li, Z.-T.; Stein, P. C.; Becher, J.; Jensen, D.; Mørk, P.; Svenstrup, N. Chem. Eur. J. 1996, 2, 624.
36. (b) Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1286.
37. (c) Ashton, P. R.; Brown, C. L.; Chrystal, E. J. T.; Goodnow, T.; Kaifer, A. E.; Parry, K. P.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F. ; Williams, D. J. J. Chem. Soc., Chem. Commun. 1991, 634.
38. No detectable absorbance was exhibited in the visible range at [1a] (=[2a]) = 0.016 M.
39. This binding pattern requires a folding conformation for the monomers. Simple monomers such as 1b and 2b might also form complexes through linear, unfolded conformation, which, however, possess less donor-acceptor interaction sites than the proposed zipper-featured motif.