A molecular knot with twelve amide groups - One-step synthesis, crystal structure, chirality

Angewandte Chemie - International Edition

Volumn 39, Issue 9, 2000, Pages 1616-1618

  Safarowsky, Oliver ^a   Nieger, Martin ^a   Fröhlich, Roland ^b   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Catenanes; Molecular knots; Molecular recognition; Rotaxanes; Self assembly

Indexed keywords

AMIDE; CATENANE; ROTAXANE;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CYCLIZATION; HYDROGEN BOND; MOLECULAR RECOGNITION; MOLECULE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034595332     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000502)39:9<1616::AID-ANIE1616>3.0.CO;2-Y     Document Type: Article

References (29)

1. Molecular Catenanes, Rotaxanes and Knots, A Journey Through the World of Molecular Topology (Eds.: J.-P. Sauvage, C. Dietrich-Buchecker), Wiley-VCH, 1999;
2. b) G. Schill, Catenanes, Rotaxanes, and Knots, Academic Press, New York, 1971.
3. Historically first knot synthesis: C. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1989, 101, 192-194; Angew. Chem. Int. Ed. Engl. 1989, 28, 189-201.
4. Historically first knot synthesis: C. Dietrich-Buchecker, J.-P. Sauvage, Angew. Chem. 1989, 101, 192-194; Angew. Chem. Int. Ed. Engl. 1989, 28, 189-201.
5. Review: N. C. Seeman, Acc. Chem. Res. 1997, 30, 357-363.
6. P. R. Ashton, O. A. Matthews, S. Menzer, F. M. Raymo, N. Spencer, J. F. Stoddart, D. J. Williams, Liebigs Ann. 1997, 2485-2494.
7. O. Safarowsky, H. Vogel, F. Vögtle, Eur. J. Org. Chem. 2000, 499-505.
8. C. A. Hunter, D. H. Purvis, Angew. Chem. 1992, 104, 779-782; Angew. Chem. Int. Ed. Engl. 1992, 31, 792-795; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311.
9. C. A. Hunter, D. H. Purvis, Angew. Chem. 1992, 104, 779-782; Angew. Chem. Int. Ed. Engl. 1992, 31, 792-795; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311.
10. C. A. Hunter, D. H. Purvis, Angew. Chem. 1992, 104, 779-782; Angew. Chem. Int. Ed. Engl. 1992, 31, 792-795; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311.
11. C. A. Hunter, D. H. Purvis, Angew. Chem. 1992, 104, 779-782; Angew. Chem. Int. Ed. Engl. 1992, 31, 792-795; F. J. Carver, C. A. Hunter, R. J. Shannon, J. Chem. Soc. Chem. Commun. 1994, 1277-1280; C. A. Hunter, J. Am. Chem. Soc. 1992, 114, 5303-5311.
12. O. Safarowsky, F. Vögtle, unpublished results.
13. a) A. Mohry, M. Nieger, F. Vögtle, Chirality 2000, 12, 76-83;
14. b) C. Reuter, C. Seel, M. Nieger, F. Vögtle, Helv. Chim. Acta 2000, 83, 641-649.
15. T. Dünnwald, R. Jäger, F. Vögtle, Chem. Eur. J. 1997, 3, 2043-2051; A. Mohry, H. Schwierz, F. Vögtle, Synthesis 1999, 10, 1753-1758.
16. T. Dünnwald, R. Jäger, F. Vögtle, Chem. Eur. J. 1997, 3, 2043-2051; A. Mohry, H. Schwierz, F. Vögtle, Synthesis 1999, 10, 1753-1758.
17. 2) was 0.485 with a conventional R(F) = 0.177 (for 25 159 reflections with I > 2σ(1)) for 2359 parameters and 1064 restraints. Approximately 30% of the structure consists of partly disordered solvent, for which the hydrogen atoms cannot be localized. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-139 484. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam. ac.uk).
18. a) G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467;
19. b) G. M. Sheldrick, Universität Göttingen, 1990.
20. S. Ottens-Hildebrandt, S. Meier, W. Schmidt, F. Vögtle, Angew. Chem. 1994, 106, 1818-1821; Angew. Chem. Int. Ed. Engl. 1994, 33, 1767-1770.
21. S. Ottens-Hildebrandt, S. Meier, W. Schmidt, F. Vögtle, Angew. Chem. 1994, 106, 1818-1821; Angew. Chem. Int. Ed. Engl. 1994, 33, 1767-1770.
22. C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; C. Seel, A. H. Parham, O. Safarowsky, G. M. Hübner, F. Vögtle, J. Org. Chem. 1999, 64, 7236-7242; see also W. Clegg, C. Gimenez-Saiz, D. A. Leigh, A. M. Murphy, M. Z. Slawin, S. J. Teat, J. Am. Chem. Soc. 1999, 121, 4124-4129.
23. C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; C. Seel, A. H. Parham, O. Safarowsky, G. M. Hübner, F. Vögtle, J. Org. Chem. 1999, 64, 7236-7242; see also W. Clegg, C. Gimenez-Saiz, D. A. Leigh, A. M. Murphy, M. Z. Slawin, S. J. Teat, J. Am. Chem. Soc. 1999, 121, 4124-4129.
24. C. Seel, F. Vögtle, Chem. Eur. J. 2000, 6, 21-24; C. Seel, A. H. Parham, O. Safarowsky, G. M. Hübner, F. Vögtle, J. Org. Chem. 1999, 64, 7236-7242; see also W. Clegg, C. Gimenez-Saiz, D. A. Leigh, A. M. Murphy, M. Z. Slawin, S. J. Teat, J. Am. Chem. Soc. 1999, 121, 4124-4129.
25. The X-ray crystal structure analysis shows clearly that the loop is helically wound, but that it only reveals a low pitch and is additionally held together by hydrogen bonds at the crossing points. Thus, this concave template resembles the macrocycles of type 3 used hitherto.
26. C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 43, 10547-10548; C. Reuter, A. Mohry, A. Sobanski, F. Vögtle, Chem. Eur. J. 2000, 6, in press.
27. C. Yamamoto, Y. Okamoto, T. Schmidt, R. Jäger, F. Vögtle, J. Am. Chem. Soc. 1997, 119, 43, 10547-10548; C. Reuter, A. Mohry, A. Sobanski, F. Vögtle, Chem. Eur. J. 2000, 6, in press.
28. Whether an "inverse synthetic route" (starting from isophthalic acid dichloride and the pyridine amide corresonding to 2) also yields molecular knots is currently under examination: A. Hünten, F. Vögtle, unpublished results.
29. J.-P. Sauvage, A. von Zelewsky, J. Becher, A. M. Brouwer, F. Vögtle, co-operation planned in the European CERC 3 program.