Self-assembly of chiral molecular polygons

Journal of the American Chemical Society

Volumn 125, Issue 27, 2003, Pages 8084-8085

  Jiang, Hua ^a   Lin, Wenbin ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; COLUMN CHROMATOGRAPHY; CONFORMATION; MICROANALYSIS; MOLECULAR DYNAMICS; MOLECULE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

EID: 0038682728     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034402t     Document Type: Article

References (26)

1. Lehn, J.-M. Supramolecular Chemistry, Concepts and Perspectives; VCH: New York, 1995.
2. (a) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502.
3. (b) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853.
4. (c) Fujita, M. Chem. Soc. Rev. 1998, 27, 417.
5. (d) Dinolfo, P. H.; Hupp, J. T. Chem. Mater. 2001, 13, 3113.
6. (e) Holliday, B. J.; Mirkin, C. A. Angew. Chem., Int. Ed. 2001, 40, 2022.
7. (f) Onitsuka, K.; Yamamoto, S.; Takahashi, S. Angew. Chem. Int. Ed. 1999, 38, 174.
8. (a) Hasenknopf, B.; Lehn, J.-M.; Boumediene.; N.; Dupont-Gervais, A.; van Dorsselaer, A.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956.
9. (b) Saalfrank, R. W.; Bernt, I.; Uller, E.; Hampel, F. Angew. Chem., Int. Ed. Engl. 1997, 36, 2482.
10. (c) Stang, P. J.; Persky, N.; Manna, J. J. Am. Chem. Soc. 1997, 119, 4777.
11. (d) Lai, S. W.; Cheung, K. K.; Chan, M. C.; Che, C. M. Angew. Chem., Int. Ed. 1998, 37, 182.
12. (e) Mamula, O.; von Zelewsky, A.; Bernardinelli, G. Angew. Chem., Int. Ed. 1998, 37, 289.
13. (f) Newkome, G. R.; Cho, T. J.; Moorefield, C. N.; Baker, G. R.; Cush, R.; Russo, P. S. Angew Chem., Int. Ed. 1999, 38, 3717.
14. (g) Matsumoto, N.; Motoda, Y.; Matsuo, T.; Nakashima, T.; Re, N.; Dahan, F.; Tuchagues, J.-P. Inorg. Chem. 1999, 38, 1165.
15. (h) Ali, M. M.; MacDonnell, F. A. J. Am. Chem. Soc. 2000, 122, 11527.
16. Hasenknopf, B.; Lehn, J.-M.; Baum, G.; Kneisel, B. O.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 1838.
17. Grossmann, B.; Heinze, J.; Herdtweck, E.; Köhler, F. H.; Nöth, H.; Schwenk, H.; Spiegler, M.; Wachter, W.; Weber, B. Angew. Chem., hit. Ed. Engl. 1997, 36, 387.
18. Jones, P. L.; Byrom, K, J.; Jeffery, J. C.; McCleverty, J. A.; Ward, M. D. J. Chem. Soc., Chem. Commun. 1997, 1361.
19. (a) Lee, S. J.; Lin, W. J. Am. Chem. Soc. 2002, 124, 4554.
20. (b) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948.
21. Jiang, H.; Hu, A.; Lin, W. Chem. Commun. 2003, 96.
22. These results are in stark contrast with those of previously reported linear polymers which were synthesized under more forcing conditions. See: Onitsuka, K.; Harada, Y.; Takei, F.; Takahashi, S. Chem. Commun. 1998, 643.
23. 2 (3:2:2 v/v/v) are 0.63, 0,47, 0.35, 0.31, 0.27, and 0.24, respectively. The yields were calculated on the basis of the starting materials, while linear oligomeric byproducts stay in the baseline.
24. +),
25. 2, consistent with the more conjugated nature of 1-6. See ref 8.
26. (b) Yam, V. W.-W. Acc. Chem. Res. 2002, 35, 555.