A "teflon-footed" resorcinarene: A hexameric capsule in fluorous solvents and fluorophobic effects on molecular encapsulation

Angewandte Chemie - International Edition

Volumn 46, Issue 34, 2007, Pages 6442-6445

  Shimizu, Shoichi ^a   Kiuchi, Toshiyuki ^a   Pan, Na ^a  

^a NIHON UNIVERSITY   (Japan)

Author keywords

Calixarenes; Perfluorinated solvents; Self assembly; Solvent effects; Supramolecular chemistry

Indexed keywords

FLUORINATION; MOLECULAR MODELING; ORGANIC SOLVENTS; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY;

CALIXARENES; PERFLUORINATED SOLVENTS; RESORCINARENE; SOLVENT EFFECTS;

OLIGOMERS;

EID: 34548318813     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702344     Document Type: Article

References (49)

1. For reviews, see a) J. Rebek, Jr., Angew. Chem. 2005, 117, 2104-2115;
2. Angew. Chem. Int. Ed. 2005, 44, 2068-2078;
3. b) M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 368-378;
4. c) M. Hof, S. L. Craig, C. Nuckolls, J. Rebek, Jr., Angew. Chem. 2002, 114, 1556-1578;
5. Angew. Chem. Int. Ed. 2002, 41, 1488-1508;
6. d) M. M. Conn, J. Rebek, Jr., Chem. Rev. 1997, 97, 1647-1668.
7. For examples, see a) E. S. Barrett, T. J. Dale, J. Rebek, Jr., J. Am. Chem. Soc. 2007, 129, 3818-3819;
8. b) M. W. Heaven, G. W. V. Cave, R. M. McKinlay, J. Antesberger, S. J. Dalgarno, P. K. Thallapally, J. L. Atwood, Angew. Chem. 2006, 118, 6367-6370;
9. Angew. Chem. Int. Ed. 2006, 45, 6221-6224;
10. c) O. Ugono, K. T. Holman, Chem. Commun. 2006, 2144-2146;
11. d) L. Avram, Y. Cohen, Org. Lett. 2006, 8, 219-222;
12. e) T. Evan-Salem, I. Baruch, L. Avram, Y. Cohen, L. C. Palmer, J. Rebek, Jr., Proc. Natl. Acad. Sci. USA 2006, 103, 12 296-12 300;
13. f) L. C. Palmer, J. Rebek, Jr., Org. Lett. 2005, 7, 787-789;
14. g) L. Avram, Y. Cohen, J. Am. Chem. Soc. 2004, 126, 11 556-11 563;
15. h) M. Yamanaka, A. Shivanyuk, J. Rebek, Jr., J. Am. Chem. Soc. 2004, 126, 2939-2943;
16. i) A. Shivanyuk, J. Rebek, Jr., J. Am. Chem. Soc. 2003, 125, 3432-3433;
17. j) L. Avram, Y. Cohen, Org. Lett. 2003, 5, 3329-3332;
18. k) L. Avram, Y. Cohen, J. Am. Chem. Soc. 2002, 124, 15 148-15 149;
19. l) I. Philip, A. E. Kaifer, J. Am. Chem. Soc. 2002, 124, 12 678-12 679;
20. m) L. Avram, Y. Cohen, Org. Lett. 2002, 4, 4365-4368;
21. n) O. Hayashida, A. Shivanyuk, J. Rebek, Jr., Angew. Chem. 2002, 114, 3573-3576;
22. Angew. Chem. Int. Ed. 2002, 41, 3423-3426;
23. o) A. Shivanyuk, J. Rebek, Jr., Chem. Commun. 2001, 2424-2425.
24. L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469-472.
25. For reviews, see a) A. Lützen, Angew. Chem. 2005, 117, 1022-1025;
26. Angew. Chem. Int. Ed. 2005, 44, 1000-1002;
27. b) M. Yoshizawa, M. Fujita, Pure Appl. Chem. 2005, 77, 1107-1112.
28. For reviews, see a) J. A. Gladysz, D. P. Curran, I. T. Horváth, Handbook of Fluorous Chemistry, Wiley-VCH, Weinheim, 2004;
29. b) P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004, pp. 171-202;
30. c) N. C. Yoder, K. Kumar, Chem. Soc. Rev. 2002, 31, 335-341;
31. d) N. C. Yoder, D. Yüksel, L. Dafik, K. Kumar, Curr. Opin. Chem. Biol. 2006, 10, 576-583.
32. a) K. E. Myers, K. Kumar, J. Am. Chem. Soc. 2000, 122, 12 025-12 026;
33. b) G. Johansson, V. Percec, G. Ungar, J. P. Zhou, Macromolecules 1996, 29, 646-660;
34. c) V. Percec, G. Johansson, G. Ungar, J. Zhou, J. Am. Chem. Soc. 1996, 118, 9855-9866.
35. S. Buscemi, A. Pace, A. P. Piccionello, S. Pappalardo, D. Garozzo, T. Pilati, G. Gattuso, A. Pappalardo, I. Pisagatti, M. F. Parisi, Tetrahedron Lett. 2006, 47, 9049-9052.
36. a) O. M. Martin, S. Mecozzi, Tetrahedron 2007, 63, 5539-5547;
37. b) O. M. Martin, L. Yu, S. Mecozzi, Chem. Commun. 2005, 4964-4966;
38. c) O. M. Martin, L. Yu, S. Mecozzi, Supramol. Chem. 2005, 17, 9-15.
39. W.-Y. Huang, J.-T. Liu, Chin. J. Chem. 1993, 11, 370-375.
40. C. Redshaw, M. R. J. Elsegood, Chem. Commun. 2005, 5056-5058.
41. C. J. M. Stirling, F. Davis (Univ. Sheffield), WO 9739077, 1997 [Chem. Abstr. 1998, 128, 4895].
42. M. Wende, F. Seidel, J. A. Gladysz, J. Fluorine Chem. 2003, 124, 45-54.
43. G. Zweifel, N. R. Ayyangar, H. C. Brown, J. Am. Chem. Soc. 1963, 85, 2072-2076.
44. C. Rocaboy, W. Bauer, J. A. Gladysz, Eur. J. Org. Chem. 2000, 2621-2628.
45. L. Abis, E. Dalcanale, A. Du vosel, S. Spera, J. Chem. Soc. Perkin Trans. 2 1990, 2075-2080.
46. F were measured after two ultrasonic irradiation of two minutes each in this study.
47. 8.
48. K. Kobayashi, Y. Asakawa, Y. Kikuchi, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1993, 115, 2648-2654.
49. A. S. Mecozzi, J. Rebek, Jr., Chem. Eur. J. 1998, 4, 1016-1022.