Covalently linked multi-calixarenes

Tetrahedron

Volumn 54, Issue 34, 1998, Pages 10053-10068

  Mogck, O ^a   Parzuchowski, P ^b   Nissinen, M ^c   Bohmer V ^a   Rokicki, G ^b   Rissanen, K ^c  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; DENDRIMER;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; COVALENT BOND; CRYSTAL STRUCTURE; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

ARENE;

EID: 0032552109     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00594-8     Document Type: Article

References (40)

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2. 2. For examples of complementary calixarene assemblies see: a) K. Kok, K. Araki, S. Shinkai, Tetrahedron Lett., 1994, 35, 8255-8258;
3. b) R.H. Vreekamp, W. Verboom, D.N. Reinhoudt, J. Org. Chem. 1996, 61, 4282-4288;
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5. 3. For examples of self complementary calixarene assemblies see: a) O. Struck, W. Verboom, W.J.J. Smeets, A.L. Spek, D.N. Reinhoudt, J. Chem. Soc., Perkin Trans. 2, 1997, 223-227;
6. b) A. Arduini, L. Domiano, L. Ogliosi, A. Pochini, A. Secchi, R. Ungaro, J. Org. Chem., 1997, 62, 7866-7868;
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9. e) K.D. Shimizu, J. Rebek Jr., Proc. Natl. Acad. Sci. USA, 1995, 92, 12403-12407;
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14. 4. This reversible formation, which allows for the intrinsic correction of wrong connections may be considered as a fundamental condition for self-assembly "reactions".
15. 5. O. Mogck, V. Böhmer, W. Vogt, Tetrahedron, 1996, 52, 8489-8496.
16. 6. For the first macrocyclic triple calix[4]renes see: a) D. Kraft, J.-D. van Loon, M. Owens, W. Verboom, W. Vogt, M.A. McKervey, V. Böhmer, D.N. Reinhoudt, Tetrahedron Lett., 1990, 31, 4941-4944;
17. b) P.D. Beer, A.D. Keefe, A.M.Z. Slawin, D.J. Wiliams, J. Chem. Soc., Dalton Trans., 1990, 3675-3682.
18. 7. For examples of triple calixarenes see: a) X. Delaigue, M. W. Hosseini, R. Graff, J.-P. Kintzinger, J. Raya, Tetrahedron Lett., 1994, 35, 1711-1714;
19. b) A. Ikeda, S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 2375-2378;
20. c) I. Higler, W. Verboom, F.C.J.M. Veggel, F. de Jong, D.N. Reinhoudt, Liebigs Ann./Recueil, 1997, 1577-1586;
21. d) P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron, 1996, 52, 12399-12408;
22. e) M.A. McKervey, M. Pitarch, Chem. Commun., 1996, 1689-1690.
23. 8. For convenience we will use the expressions double-and triple-but tetra-, penta-calixarenes etc., indicating thus the number of calixarene units per molecule.
24. 9. a) P. Lhotak, S. Shinkai, Tetrahedron, 1995, 51, 7681-7696;
25. b) P. Lhotak, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron, 1996, 52, 12399-12408;
26. c) M.A. McKervey, M. Pitarch, Chemm. Commun. 1996, 1689-1690.
27. 10. P. Timmermann, W. Verboom, F.C.J.M. van Veggel, W.P. van Hoorn, D.N. Reinhoudt, Angew. Chem., Int. Ed. Engl., 1994, 33, 1292-1295.
28. 11. A. Ikeda, S. Shinkai, J. Chem. Soc., Chem. Commun., 1994, 2375-2378.
29. 12. R.A. Jakobi, V. Böhmer, C. Grüttner, D. Kraft, W. Vogt, New. J. Chem., 1996, 20, 493-501.
30. 13. C. Fischer, M. Nieger, O. Mogck, V. Böhmer, R. Ungaro, F. Vögtle, Eur. J. Org. Chem., 1998, 1, 155-161.
31. 14. For an amide bridged tetra calix[4]arene based on a calix[4]arene diacid see: M. Jorgensen, M. Larsen, P. Sommer-Larsen, W.B. Petersen, H. Eggert, J. Chem. Soc., Perkin Trans. 1, 1997, 2851-2855.
32. 15. For a first example see: W. Verboom, A. Durie, R.J.M. Egberink, Z. Asfari, D.N. Reinhoudt, J. Org. Chem., 1992, 57, 1313-1316.
33. - by a similar double calixarene see: P.D. Beer, J.B. Cooper, Chem. Commun., 1998, 129-130.
34. 17. S. Pappalardo, G. Ferguson, J.F. Gallagher, J. Org. Chem., 1992, 57, 7102-7109.
35. 18. A. Arduini, A. Pochini, S. Reverberi, R. Ungaro, G.D. Andreetti, F. Ugozzoli, Tetrahedron, 1986, 42, 2089-2100.
36. 19. G. Barrett, V. Böhmer, G. Ferguson, J.F. Gallagher, S.J. Harris, R.G. Leonard, M.A. McKervey, M. Owens, M. Tabatabai, A. Vierengel, W. Vogt, J. Chem. Soc., Perkin Trans. 2, 1992, 1595-1601.
37. +. This is evidenced for instance by amide signals in the range of 8.92-8.72 ppm in addition to the signal at 8.84 ppm found for 10. The observed spectra demonstrate, however, that the spectroscopic properties of the outer calix[4]arenes are nearly independent from each other.
38. 21. For the use of calix[4]arenes as cores for dendrimers see also: G. Ferguson, J.F. Gallagher, M.A. McKervey, E. Madigan, J. Chem. Soc., Perkin Trans. 1, 1996, 599-602.
39. 22. G.M. Sheldrick, Acta Cryst. 1990, A46, 467.
40. 23. G.M. Sheldrick, SHELXL-97 - A program for crystal structure refinement, 1997, University of Göttingen, Germany.