Supramolecular amphiphiles: Spontaneous formation of vesicles triggered by formation of a charge-transfer complex in a host

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4474-4476

  Jeon, Young Jin ^a   Bharadwaj, Parimal K ^a   Choi, SooWhan ^a   Lee, Jae Wook ^a   Kim, Kimoon ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Charge transfer; Cucurbituril; Host guest systems; Supramolecular chemistry; Vesicles

Indexed keywords

CHARGE TRANSFER; TRANSMISSION ELECTRON MICROSCOPY;

OXIDIZING AGENTS;

SUPRAMOLECULAR CHEMISTRY;

AMPHOPHILE; GAMMA CYCLODEXTRIN; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; COMPLEX FORMATION; IMAGE ANALYSIS; ION CHANNEL; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; SUPRAMOLECULAR CHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY;

EID: 85034319483     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4500::AID-ANIE4500>3.0.CO;2-N     Document Type: Article

References (67)

1. a) J. H. Fendler, Membrane Mimetic Chemistry, Wiley, New York, 1982;
2. b) T. Kunitake, Angew. Chem. 1992, 104, 692; Angew. Chem. Int. Ed. Engl. 1992, 31, 709.
3. b) T. Kunitake, Angew. Chem. 1992, 104, 692; Angew. Chem. Int. Ed. Engl. 1992, 31, 709.
4. a) Y. Tanaka, M. Miyachi, Y. Kokube, Angew. Chem. 1999, 111, 565; Angew. Chem. Int. Ed. 1999, 38, 504;
5. a) Y. Tanaka, M. Miyachi, Y. Kokube, Angew. Chem. 1999, 111, 565; Angew. Chem. Int. Ed. 1999, 38, 504;
6. b) Y. Einaga, O. Sato, T. Iyoda, A. Fujishima, K. Hashimoto, J. Am. Chem. Soc. 1999, 121, 3745;
7. c) Q. Cheng, T. Peng, R. C. Stevens, J. Am. Chem. Soc. 1999, 121, 6767;
8. d) Y. R. Vandenberg, B. D. Smith, M. N. Pérez-Paýn, A. P. Davis, J. Am. Chem. Soc. 2000, 122, 3252;
9. e) S. Kolusheva, T. Shahal, R. Jelinek, J. Am. Chem. Soc. 2000, 122, 776;
10. f) A. Veronese, P. L. Luisi, J. Am. Chem. Soc. 1998, 120, 2662;
11. g) T. Renkes, H. J. Schäfer, P. M. Siemens, E. Neumann, Angew. Chem. 2000, 112, 2566; Angew. Chem. Int. Ed. 2000, 39, 2515;
12. g) T. Renkes, H. J. Schäfer, P. M. Siemens, E. Neumann, Angew. Chem. 2000, 112, 2566; Angew. Chem. Int. Ed. 2000, 39, 2515;
13. h) P. Ghosh, S. Sengupta, P. K. Bharadwaj, Langmuir 1998, 14, 5712;
14. i) P. Bandyopadhyay, P. K. Bharadwaj, Langmuir 1998, 14, 7537.
15. a) B. J. Ravoo, R. Darcy, Angew. Chem. 2000, 112, 4494; Angew. Chem. Int. Ed. 2000, 39, 4324;
16. a) B. J. Ravoo, R. Darcy, Angew. Chem. 2000, 112, 4494; Angew. Chem. Int. Ed. 2000, 39, 4324;
17. b) M. Brettreich, S. Burghardt, C. Böttler, T. Bayerl, S. Bayerl, A. Hirsch, Angew. Chem. 2000, 112, 1915; Angew. Chem. Int. Ed. 2000, 39, 1845;
18. b) M. Brettreich, S. Burghardt, C. Böttler, T. Bayerl, S. Bayerl, A. Hirsch, Angew. Chem. 2000, 112, 1915; Angew. Chem. Int. Ed. 2000, 39, 1845;
19. c) A. M. Cassell, C. C. Asplund, J. M. Tour, Angew. Chem. 1999, 111, 2565; Angew. Chem. Int. Ed. 1999, 38, 2403;
20. c) A. M. Cassell, C. C. Asplund, J. M. Tour, Angew. Chem. 1999, 111, 2565; Angew. Chem. Int. Ed. 1999, 38, 2403;
21. d) M. Hetzer, H. Clausen-Schaumann, S. Bayerl, T. M. Bayerl, X. Camps, O. Vostrowsky, A. Hirsch, Angew. Chem. 1999, 111, 2103; Angew. Chem. Int. Ed. 1999, 38, 1962;
22. d) M. Hetzer, H. Clausen-Schaumann, S. Bayerl, T. M. Bayerl, X. Camps, O. Vostrowsky, A. Hirsch, Angew. Chem. 1999, 111, 2103; Angew. Chem. Int. Ed. 1999, 38, 1962;
23. e) S. Zhou, C. Burger, B. Chu, M. Sawamura, N. Nagahama, M. Toganoh, U. E. Hackler, H. Isobe, E. Nakamura, Science 2001, 291, 1944.
24. a) V. Marchi-Artzner, L. Jullien, T. Gulik-Krzywicki, J.-M. Lehn, Chem. Commun. 1997, 117;
25. b) F. Ilhan, T H. Galow, M. Gray, G. Clavier, V. M. Rotello, J. Am. Chem. Soc. 2000, 122, 5895.
26. For reviews of cucurbituril, see a) W. L. Mock, Comprehensive Supramolecular Chemistry, Vol. 2, (Ed.: F. Vögtle) Pergamon, Oxford, 1996, p477; b) P. Cintas, J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 17, 205.
27. For reviews of cucurbituril, see a) W. L. Mock, Comprehensive Supramolecular Chemistry, Vol. 2, (Ed.: F. Vögtle) Pergamon, Oxford, 1996, p477; b) P. Cintas, J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 17, 205.
28. a) Y.-M. Jeon, J. Kim, D. Whang, K. Kim, J. Am. Chem. Soc. 1996, 118, 9790;
29. b) D. Whang, J. Heo, J. H. Park, K. Kim, Angew. Chem. 1998, 110, 83; Angew. Chem. Int. Ed. 1998, 37, 78;
30. b) D. Whang, J. Heo, J. H. Park, K. Kim, Angew. Chem. 1998, 110, 83; Angew. Chem. Int. Ed. 1998, 37, 78;
31. c) H.-J. Kim, J. Heo, W. S. Jeon, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 1574; Angew. Chem. Int. Ed. 2001, 40, 1526.
32. c) H.-J. Kim, J. Heo, W. S. Jeon, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 1574; Angew. Chem. Int. Ed. 2001, 40, 1526.
33. a) D. Whang, Y.-M. Jeon, J. Heo, K. Kim, J. Am. Chem. Soc. 1996, 118, 11333;
34. b) D. Whang, K. Kim, J. Am. Chem. Soc. 1997, 119, 451;
35. c) D. Whang, K.-M. Park, J. Heo, K. Kim, J. Am. Chem. Soc. 1998, 120, 4899;
36. d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638;
37. d) S.-G. Roh, K.-M. Park, G.-J. Park, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 1999, 111, 672; Angew. Chem. Int. Ed. 1999, 38, 638;
38. e) E. Lee, J. Heo, K. Kim, Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699;
39. e) E. Lee, J. Heo, K. Kim, Angew. Chem. 2000, 112, 2811; Angew. Chem. Int. Ed. 2000, 39, 2699;
40. f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399;
41. f) E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, Angew. Chem. 2001, 113, 413; Angew. Chem. Int. Ed. 2001, 40, 399;
42. g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746;
43. g) J. W. Lee, Y. H. Ko, S.-H. Park, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 768; Angew. Chem. Int. Ed. 2001, 40, 746;
44. h) K.-M. Park, D. Whang, E. Lee, J. Heo, K. Kim, Chem. Eur. J. 2002, 8, 498;
45. i) K.-M. Park, S.-Y. Kim, J. Heo, D. Whang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2002, 124, 2140;
46. j) K. Kim, Chem. Soc. Rev. 2002, 31, 96.
47. J. Kim, I.-S. Jung, S.-Y., Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, K. Kim, J. Am. Chem. Soc. 2000, 122, 540.
48. a) H.-J. Kim, J. Heo, W. S. Jeon, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 1574; Angew. Chem. Int. Ed. 2001, 40, 1526;
49. a) H.-J. Kim, J. Heo, W. S. Jeon, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 1574; Angew. Chem. Int. Ed. 2001, 40, 1526;
50. b) S.-Y. Kim, I.-S. Jung, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 2177; Angew. Chem. Int. Ed. 2001, 40, 2119;
51. b) S.-Y. Kim, I.-S. Jung, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 2177; Angew. Chem. Int. Ed. 2001, 40, 2119;
52. c) S. Y. Jon, Y. H. Ko, S. H. Park, H.-J. Kim, K. Kim, Chem. Commun. 2001, 19, 1938;
53. d) H.-J. Kim, W. S. Jeon, Y. H. Ko, K. Kim, Proc. Natl. Acad. Sci. USA, 2002, 99, 5007.
54. a) A. Day, A. P. Arnold, R. J. Blanch, B. Snushall, J. Org. Chem. 2001, 66, 8094;
55. b) R. J. Blanch, A. J. Sleeman, T. J. White, A. P. Arnold, A. I. Day, Nano Lett. 2002, 2, 147;
56. c) A. I. Day, R. J. Blanch, A. P. Arnold, S. Lorenzo, G. R. Lewis, I. Dance, Angew. Chem. 2002, 114, 285; Angew. Chem. Int. Ed. 2002, 41, 275;
57. c) A. I. Day, R. J. Blanch, A. P. Arnold, S. Lorenzo, G. R. Lewis, I. Dance, Angew. Chem. 2002, 114, 285; Angew. Chem. Int. Ed. 2002, 41, 275;
58. d) C. Marqiez, W. M. Nau, Angew. Chem. 2001, 113, 4515; Angew. Chem. Int. Ed. 2001, 40, 4387.
59. d) C. Marqiez, W. M. Nau, Angew. Chem. 2001, 113, 4515; Angew. Chem. Int. Ed. 2001, 40, 4387.
60. a) Y. Lei, J. K. Hurst, J. Phys. Chem. 1991, 95, 7918;
61. b) K. L. Kovacs, A. Der, Biochimie 1986, 68, 211.
62. 2+].
63. See Supporting Information.
64. a) A. Diaz, P. A. Quintela, J. M. Schuette, A. E. Kaifer, J. Phy. Chem. 1988, 92, 3537;
65. b) Y. Lee, C. Lee, Bull. Korean Chem. Soc. 1999, 20, 1.
66. Preparation of the dye-entrapped vesicles and calculation of the dye-entrapped volume were carried out by conventional experimental procedures used for liposomes: R. C. C. New, Liposomes: A practical approach, Oxford University, Oxford, 1990.
67. Addition of CAN to an aqueous solution of sulforhodamine G results in immediate quenching of its fluorescence as a consequence of the rapid oxidation of the dye; therefore, the release of the dye from the dye-entrapped vesicle triggered by CAN could not be monitored.