Nanoscale-container structures and their host - Guest properties

Angewandte Chemie - International Edition

Volumn 39, Issue 6, 2000, Pages 1076-1079

  Tucci, Fabio C ^a   Renslo, Adam R ^a   Rudkevich, Dmitry M ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Cavitands; Host guest chemistry; Hydrogen bonds; Molecular recognition; Nanostructures

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULE; NANOPARTICLE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034678010     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1076::AID-ANIE1076>3.0.CO;2-E     Document Type: Article

References (47)

1. a) J. A. Bryant, M. T. Blanda, M. Vincenti, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2167-2172;
2. b) J. C. Sherman, C. B. Knobler, D. J. Cram, J. Am. Chem. Soc. 1991, 113, 2194-2204; reviews;
3. c) D. J. Cram, J. M. Cram, Container Molecules and their Guests, Royal Society of Chemistry, Cambridge, 1994, pp. 131-148;
4. d) A. Collet, J.-P. Dutasta, B. Lozach, J. Canceill, Top. Curr. Chem. 1993, 165, 103-129;
5. e) A. Jasat, J. C. Sherman, Chem. Rev. 1999, 99, 931-967.
6. a) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668;
7. b) J. de Mendoza, Chem. Eur. J. 1998, 4, 1373-1377;
8. c) D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200;
9. d) T. Kusukawa, M. Fujita, Angew. Chem. 1998, 110, 3327-3329; Angew. Chem. Int. Ed. 1998, 37, 3142-3144;
10. d) T. Kusukawa, M. Fujita, Angew. Chem. 1998, 110, 3327-3329; Angew. Chem. Int. Ed. 1998, 37, 3142-3144;
11. e) T. Kusukawa, M. Fujita, J. Am. Chem. Soc. 1999, 121, 1397-1398.
12. a) D. J. Cram, M. E. Tanner, C. B. Knobler, J. Am. Chem. Soc. 1991, 113, 7717-7727;
13. b) D. J. Cram, M. T. Blanda, K. Paek, C. B. Knobler, J. Am. Chem. Soc. 1992, 114, 7765-7773;
14. c) T. A. Robbins, C. B. Knobler, D. R. Bellew, D. J. Cram, J. Am. Chem. Soc. 1994, 116, 111-122; slow decomplexation at 295 K;
15. d) D. J. Cram, R. Jaeger, K. Deshayes, J. Am. Chem. Soc. 1993, 115, 10111-10116.
16. Reviews: a) D. J. Cram, Science 1983, 219, 1177-1183;
17. b) D. M. Rudkevich, J. Rebek, Jr., Eur. J. Org. Chem. 1999, 1991-2005.
18. a) D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 12216-12225;
19. b) D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr. J. Am. Chem. Soc. 1997, 119, 9911-9912;
20. c) S. Ma, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 2761-2764; Angew. Chem. Int. Ed. 1999, 38, 2600-2602.
21. c) S. Ma, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 2761-2764; Angew. Chem. Int. Ed. 1999, 38, 2600-2602.
22. Earlier examples of unimolecular capsules: a) R. G. Chapman, J. C. Sherman, J. Am. Chem. Soc. 1998, 120, 9818-9826;
23. b) M. S. Brody, C. A. Schalley, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1738-1742; Angew. Chem. Int. Ed. 1999, 38, 1640-1644.
24. b) M. S. Brody, C. A. Schalley, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1738-1742; Angew. Chem. Int. Ed. 1999, 38, 1640-1644.
25. For other approaches towards nanosize host-molecules, see a) P. Timmerman, K. G. A. Nierop, E. A. Brinks, W. Verboom, F. C. J. M. van Veggel, W. P. van Hoorn, D. N. Reinhoudt, Chem. Eur. J. 1995, 1, 132-143;
26. b) I. Higler, P. Timmerman, W. Verboom, D. N. Reinhoudt, J. Org. Chem. 1996, 61, 5920-5931;
27. c) I. Higler, W. Verboom, F. C. J. M. van Veggel, F. de Jong, D. N. Reinhoudt, Liebigs Ann. Chem. 1997, 1577-1586;
28. d) N. Chopra, J. C. Sherman, Angew. Chem. 1999, 111, 2109-2111; Angew. Chem. Int. Ed. 1999, 38, 1955-1957.
29. d) N. Chopra, J. C. Sherman, Angew. Chem. 1999, 111, 2109-2111; Angew. Chem. Int. Ed. 1999, 38, 1955-1957.
30. A. R. Renslo, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 7459-7460.
31. F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Org. Chem. 1999, 64, 4555-4559.
32. 3 were detected at temperatures of 240 K or lower in [D8]toluene. Complete experimental details will be published in a full paper.
33. Topologically similar bis-cavitands have been reported: D. J. Cram, L. M. Tunstad, C. B. Knobler, J. Org. Chem. 1992, 57, 528-535.
34. For the concept of molecular rulers, see S. K. Körner, F. C. Tucci, D. M. Rudkevich, T. Heinz, J. Rebek, Jr., Chem. Eur. J. 2000, 6, 187-195.
35. -1 (295 K); T. Szabo, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 6193-6194.
36. -1 (295 K); T. Szabo, G. Hilmersson, J. Rebek, Jr., J. Am. Chem. Soc. 1998, 120, 6193-6194.
37. a) D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027;
38. a) D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048; Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027;
39. b) R. Warmuth, Angew. Chem. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350.
40. b) R. Warmuth, Angew. Chem. 1997, 109, 1406-1409; Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350.
41. P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348.
42. P. Timmerman, W. Verboom, F. C. J. M. van Veggel, J. P. M. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348.
43. a) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766;
44. b) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1206-1209; Angew. Chem. Int. Ed. Engl. 1999, 38, 1136-1139;
45. b) T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. 1999, 111, 1206-1209; Angew. Chem. Int. Ed. Engl. 1999, 38, 1136-1139;
46. c) F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 4928-4929.
47. J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.