Hydrogen-bond-assisted π-stacking of shape-persistent cyclophanes

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7761-7768

  Lin, Chih Hsiu ^a   Tour, James ^a  

^a RICE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GEL FORMATION;

GELS; HYDROGEN BONDS; SUPRAMOLECULAR CHEMISTRY;

DIMERS;

CYCLOPHANE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; GEL; HYDROGEN BOND; MOLECULAR INTERACTION;

EID: 0036827596     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025723a     Document Type: Article

References (37)

1. (a) Hunter, C. A. Angew. Chem., Int. Ed. 1993, 37, 249.
2. (b) Hunter, C. A. Chem. Soc. Rev. 1994, 101.
3. (a) Schmidt-Mende, L.; Fechtenkotter, A.; Mullen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1122.
4. (b) Adam, D.; Schuhmacher, P.; Simmerer, J. Nature 1994, 371, 141.
5. (a) Tuner, D. H.; Sugimoto, N.; Freier, S. M. In Nucleic Acids; Saenger, W., Ed.; Springer-Verlag: Berlin, 1990; Subvol. C, pp 201-27.
6. (b) Freier, S. M.; Sugimoto, N.; Sinclair, A.; Alkema, D.; Nielson, T.; Kierzek, R.; Caruthers, M. H.; Turner, D. H. Biochemistry 1986, 25, 3214.
7. (c) Guckian, K.; Schweitzer, B. A.; Ren, X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D. C.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182.
8. (a) Jones, G. B.; Chapeman, B. J. Synthesis 1995, 475.
9. (b) Corey E. J.; Noe M. C. J. Am. Chem. Soc. 1996, 118, 319.
10. (a) Burly, S. K.; Pestko, G. A. Science 1985, 299, 23.
11. (b) DiNitto, J. P.; Huber, P. W. Biochemistry 2001, 40, 12645-12653.
12. (a) Whitesides, G. M.; Mathias J. P.; Seto, C. T. Science 1991, 254, 1312.
13. (b) Lawerance, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229.
14. (c) Stang, P. J. Chem. Rev. 2000, 100, 853.
15. (a) Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1992, 114, 9701.
16. (b) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019.
17. (a) Tobe, Y.; Utsumi, N.; Kawabata, K.; Naemura, K. Tetrahedron Lett. 1996, 37, 9325.
18. (a) Tobe, Y.; Utsumi, N.; Nagano, A.; Naemura, K. Angew. Chem., Int. Ed. 1998, 37, 1285.
19. (b) Tobe, Y.; Nagano, A.; Kawabata, K.; Sonoda, M.; Naemura, K. Org. Lett. 2000, 2, 3265.
20. (c) Lahiri S.; Thompson J. L.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 11315.
21. Nakamura, K.; Okubo, H.; Yamaguchi, M. Org. Lett. 2001, 3, 1097.
22. (a) Mindyuk, O. Y.; Stetzer, M. R.; Heiney, P. A.; Nelson, J. C.; Moore, J. S. Adv. Mater. 1998, 10, 1363.
23. (b) Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1994, 116, 2655.
24. Rosselli, S.; Ramminger, A.-D.; Wagner, T.; Silier, B.; Wiegand, S.; Haussler, W.; Lieser, G.; Scheumann, V.; Hoger, S. Angew. Chem., Int. Ed. 2001, 40, 3138.
25. Synthesized according to Kraus, R.; Spiteller, G. Org. Mass Spectrom. 1989, 24, 861.
26. (a) Mitchell, R. H.; Lai, Y. H.; William, R. J. Org. Chem. 1979, 44, 4733.
27. (b) Doyle, M. P.; Dellaria, J. F., Jr.; Siegfried, B.; Bishop, S. W. J. Org. Chem. 1977, 42, 3494.
28. (a) Siemsen P.; Livingston R. C.; Diederich F. Angew. Chem., Int. Ed. 2000, 39, 2632.
29. (b) Höger S.; Bonrad K.; Karcher L.; Meckenstock A.-D. J Org. Chem. 2000, 65, 1588.
30. Horman, I.; Dreux, B. Helv. Chim. Acta 1984, 67, 754.
31. The equilibrium constant at 25°C was intrapolated from the van't Hoff plot.
32. An oligoethylene glycol-alkoxyl-substituted SPC did form a dimer in acetone solution (ref 9c). However, the nature of the driving force is proposed to be solvophobic.
33. Interestingly, we discovered that thin-layer chromatography (TLC), in addition to NMR, can be used to detect the dimerization in this class of compounds. When developed on TLC plates, the monomeric cyclophane (1) showed a regular inverted-V-shaped tailing trail. In contrast, all the aggregating cyclophanes (2-4) exhibited very unusual V-shaped reverse-tailing trails. A similar phenomenon was also observed in alkyl-substituted cyclophanes (vide infra). Whether this phenomenon is the result of the π-stacking remains an open question.
34. (a) Ajayaghosh, A.; George S. J. J. Am. Chem. Soc. 2001, 123, 5148.
35. (b) Tamaru, S.; Nakamura, M.; Takeuchi, M.; Shinkai, S. Org. Lett. 2001, 3, 3723.
36. (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
37. (b) Jennings, W. B.; Farrell, B. M.; Malone, J. F. Acc. Chem. Res. 2001, 34, 885.