Programming a hydrogen-bonding code for the specific generation of a supermacrocycle

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 19, 1996, Pages 2204-2206

  Mascal, Mark ^a   Hext, Nicholas M ^a   Warmuth, Ralf ^a   Moore, Madeleine H ^b   Turkenburg, Johan P ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Channel structures; Hydrogen bonds; Self assembly

Indexed keywords

EID: 0030445476     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199622041     Document Type: Article

References (45)

1. a) M. Mascal, Contemp. Org. Synth. 1994, 1, 31;
2. b) D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229;
3. c) G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311;
4. c) G. R. Desiraju, Angew. Chem. 1995, 107, 2541; Angew. Chem. Int. Ed. Engl. 1995, 34, 2311;
5. d) J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995, and references therein.
6. a) M. C. Etter, Acc. Chem. Res. 1990, 23, 120;
7. b) J. Phys. Chem. 1991, 95, 4601;
8. c) C. B. Aakeröy, K. R. Seddon, Chem. Soc. Rev. 1993, 22, 397;
9. d) J. C. MacDonald, G. M. Whitesides, Chem. Rev. 1994, 94, 2383;
10. e) J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1687; Angew. Chem. Int. Ed. Engl. 1995, 34, 1555, and references therein.
11. e) J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1687; Angew. Chem. Int. Ed. Engl. 1995, 34, 1555, and references therein.
12. a) O. Ermer, L. Lindenberg, Helv. Chim. Acta 1991, 74, 825;
13. b) X. Wang, M. Simard, J. D. Wuest, J. Am. Chem. Soc. 1994, 116, 12119.
14. S. C. Zimmerman, F. Zeng, D. E. C. Reichert, S. V. Kolotuchin, Science 1996, 271, 1095.
15. a) D. J. Duchamp, R. E. Marsh, Acta Crystallogr. Sect. B 1969, 25, 5;
16. b) F. Garcia-Tellado, S. J. Geib, S. Goswami, A. D. Hamilton, J. Am. Chem. Soc. 1991, 113, 9265;
17. c) Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauher, ibid. 1993, 115, 5991;
18. d) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591;
19. e) S. V. Kolotuchin, E. F. Fenlon, S. R. Wilson, C. J. Loweth, S. C. Zimmerman, Angew. Chem. 1995, 107, 2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2564.
20. e) S. V. Kolotuchin, E. F. Fenlon, S. R. Wilson, C. J. Loweth, S. C. Zimmerman, Angew. Chem. 1995, 107, 2873; Angew. Chem. Int. Ed. Engl. 1995, 34, 2564.
21. J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 479.
22. J. A. Zerkowski, C. T. Seto, D. A. Wierda, G. M. Whitesides, J. Am. Chem. Soc. 1990, 112, 9025.
23. a) C. Fouquey, J.-M. Lehn, A. Levelut, Adv. Mater. 1990, 2, 254;
24. b) S. J. Geib, C. Vincent, E. Fan, A. D. Hamilton, Angew. Chem. 1993, 105, 83; Angew. Chem. Int. Ed. Engl. 1993, 32, 119.
25. b) S. J. Geib, C. Vincent, E. Fan, A. D. Hamilton, Angew. Chem. 1993, 105, 83; Angew. Chem. Int. Ed. Engl. 1993, 32, 119.
26. J. D. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, J. Am. Chem. Soc. 1996, 118, 43, and references therein.
27. a) G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1992, 254, 1312;
28. b) G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Chin, M. Mammen, D. M. Gordon, Acc. Chem. Res. 1995, 28, 37.
29. a) J. Yang, E. Fan, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1993, 115, 5314, and references therein;
30. b) Y. Yang, J.-L. Marendaz, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1994, 35, 3665.
31. a) R. Wyler, J. deMendoza, J. Rebek, Jr., Angew. Chem. 1993, 105, 1820; Angew. Chem. Int. Ed. Engl. 1993, 32, 1699;
32. a) R. Wyler, J. deMendoza, J. Rebek, Jr., Angew. Chem. 1993, 105, 1820; Angew. Chem. Int. Ed. Engl. 1993, 32, 1699;
33. b) C. Valdés, U. P. Spitz, L. M. Toledo, S. W. Kubik, J. Rebek, Jr., J. Am. Chem. Soc. 1995, 117, 12733.
34. For a related system see: N. Kimizuka, T. Kawasaki, K. Hirata, T. Kunitake, J. Am. Chem. Soc. 1995, 117, 6360.
35. a) J. A. Zerkowski, G. M. Whitesides, J. Am. Chem. Soc. 1994, 116, 4298;
36. b) J. A. Zerkowski, J. P. Mathias, G. M. Whitesides, ibid. 1994, 116, 4305;
37. c) J. P. Mathias, E. E. Simanek, J. A. Zerkowski, C. T. Seto, G. M. Whitesides, ibid. 1994, 116, 4316;
38. d) J. A. Zerkowski, C. T. Seto, G. M. Whitesides, ibid. 1992, 114, 5473.
39. A version of 3 synthesized without the tailgroup did not dissolve to an appreciable extent in any solvent.
40. Compound 3 also gave crystals of similar appearance from DMF and DMF/DMSO mixtures. The possibility that powerful H-bond accepting solvents such as these could interfere with the assembly process was considered, but the experience has been that interbase H-bonding tends to win out over competition: J.-M. Lehn, M. Mascal, A. DeCian, J. Fischer, J. Chem. Soc. Perkin Trans 2 1992, 461.
41. F = 0.1523 on 1≥ 2σ(I) data] and S = 1.723. Although the overall solution is satisfactory, we are continuing to investigate the distribution of the remaining solvent molecules. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-179-90. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: Int. code +(1223) 336-033; e-mail: teched@chemcrys.cam.ac.uk).
42. This is the first report of an all-organic molecule in this space group. Only two other molecules in 1a3̄d UK identified in a search of the Cambridge Crystallographic Database (F. H. Allen, J. E. Davies, J. J. Galloy, O. Johnson, O. Kennard, C. F. Macrae, E. M. Mitchell, G. F. Mitchell, J. M. Smith, D. G. Watson, J. Chem. Info. Comput. Sci. 1991, 31, 187).
43. J. Pranata, S. G. Wierschke, W. L. Jorgensen, J. Am. Chem. Soc. 1991, 113, 2810.
44. -3), in which they are not buoyant.
45. A. Marsh, M. Silvestri, J.-M. Lehn, Chem. Commun. 1996, 1527.