Photoresponsive molecular recognition and adhesion of vesicles in a competitive ternary supramolecular system

Chemistry - A European Journal

Volumn 17, Issue 37, 2011, Pages 10297-10303

  Nalluri, Siva Krishna Mohan ^a   Bultema, Jelle B ^b   Boekema, Egbert J ^b   Ravoo, Bart Jan ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

cyclodextrins; host guest systems; molecular recognition; photoresponsive systems; vesicles

Indexed keywords

AMPHIPHILICS; CRYOGENIC TRANSMISSION ELECTRON MICROSCOPY (CRYO-TEM); DILUTE AQUEOUS SOLUTION; HOST-GUEST SYSTEMS; INCLUSION COMPLEX; ISOTHERMAL TITRATION CALORIMETRY; NONCOVALENT; PHOTORESPONSIVE; PHOTORESPONSIVE SYSTEMS; REDISPERSIONS; SUPRAMOLECULAR SYSTEMS; TERNARY MIXTURES; THREE COMPONENT; TRANS STATE; UV IRRADIATION; VESICLES; VISIBLE IRRADIATION; WEAK INCLUSION;

ADHESION; CYCLODEXTRINS; DENSITY MEASUREMENT (OPTICAL); DISPERSIONS; DYNAMIC LIGHT SCATTERING; IRRADIATION; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; TRANSMISSION ELECTRON MICROSCOPY;

AGGLOMERATION;

ALPHA CYCLODEXTRIN DERIVATIVE; AZO COMPOUND; AZOBENZENE; BETA CYCLODEXTRIN DERIVATIVE; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PHOTOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALPHA-CYCLODEXTRINS; AZO COMPOUNDS; BETA-CYCLODEXTRINS; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; STEREOISOMERISM; WATER;

EID: 80052191757     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100789     Document Type: Article

References (77)

1. A. Heeres, C. van der Pol, M. C. A. Stuart, A. Friggeri, B. L. Feringa, J. van Esch, J. Am. Chem. Soc. 2003, 125, 14252-14253.
2. J. van Herrikhuyzen, A. Syamakumari, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2004, 126, 10021-10027.
3. H. Xu, R. Hong, T. Lu, O. Uzun, V. M. Rotello, J. Am. Chem. Soc. 2006, 128, 3162-3163.
4. O. Crespo-Biel, C. W. Lim, B. J. Ravoo, D. N. Reinhoudt, J. Huskens, J. Am. Chem. Soc. 2006, 128, 17024-17032.
5. C. F. C. Fitié, I. Tomatsu, D. Byelov, W. H. de Jeu, R. P. Sijbesma, Chem. Mater. 2008, 20, 2394-2404.
6. M. Schmittel, K. Mahata, Angew. Chem. 2008, 120, 5364-5366
7. Angew. Chem. Int. Ed. 2008, 47, 5284-5286.
8. S. K. Yang, A. V. Ambade, M. Weck, J. Am. Chem. Soc. 2010, 132, 1637-1645.
9. A. González-Campo, S. H. Hsu, L. Puig, J. Huskens, D. N. Reinhoudt, A. H. Velders, J. Am. Chem. Soc. 2010, 132, 11434-11436.
10. S. Yagai, T. Karatsu, A. Kitamura, Chem. Eur. J. 2005, 11, 4054-4063.
11. U. Kusebauch, S. A. Cadamuro, H. J. Musiol, M. O. Lenz, J. Wachtveitl, L. Moroder, C. Renner, Angew. Chem. 2006, 118, 7170-7173
12. Angew. Chem. Int. Ed. 2006, 45, 7015-7018.
13. C. J. Barrett, J. I. Mamiya, K. G. Yager, T. Ikeda, Soft Matter 2007, 3, 1249-1261.
14. T. Murase, S. Sato, M. Fujita, Angew. Chem. 2007, 119, 5225-5228
15. Angew. Chem. Int. Ed. 2007, 46, 5133-5136.
16. S. Yagai, A. Kitamura, Chem. Soc. Rev. 2008, 37, 1520-1529.
17. F. L. Callari, S. Sortino, Chem. Commun. 2008, 6179-6181.
18. M. L. Juan, J. Plain, R. Bachelot, P. Royer, S. K. Gray, G. P. Wiederrecht, ACS Nano 2009, 3, 1573-1579.
19. D. B. Liu, Y. Y. Xie, H. W. Shao, X. Y. Jiang, Angew. Chem. 2009, 121, 4470-4472
20. Angew. Chem. Int. Ed. 2009, 48, 4406-4408.
21. R. Klajn, P. J. Wesson, K. J. M. Bishop, B. A. Grzybowski, Angew. Chem. 2009, 121, 7169-7173
22. Angew. Chem. Int. Ed. 2009, 48, 7035-7039.
23. R. S. Stoll, M. V. Peters, A. Kuhn, S. Heiles, R. Goddard, M. Bühl, C. M. Thiele, S. Hecht, J. Am. Chem. Soc. 2009, 131, 357-367.
24. G. H. Clever, S. Tashiro, M. Shionoya, J. Am. Chem. Soc. 2010, 132, 9973-9975.
25. Y. Hua, A. H. Flood, J. Am. Chem. Soc. 2010, 132, 12838-12840.
26. H. Koshima, N. Ojima, H. Uchimoto, J. Am. Chem. Soc. 2009, 131, 6890-6891.
27. C. Wang, Q. Chen, F. Sun, D. Zhang, G. Zhang, Y. Huang, R. Zhao, D. Zhu, J. Am. Chem. Soc. 2010, 132, 3092-3096.
28. K. Smaali, S. Lenfant, S. Karpe, M. OÃafrain, P. Blanchard, D. Deresmes, S. Godey, A. Rochefort, J. Roncali, D. Vuillaume, ACS Nano 2010, 4, 2411-2421.
29. M. Chen, F. Besenbacher, ACS Nano 2011, 5, 1549-1555.
30. S. Venkataramani, U. Jana, M. Dommaschk, F. D. Sönnichsen, F. Tuczek, R. Herges, Science 2011, 331, 445-448.
31. M. Higuchi, A. Takizawa, T. Kinoshita, Y. Tsujita, Macromolecules 1987, 20, 2888-2892.
32. H. Sakai, A. Matsumura, S. Yokoyama, T. Saji, M. Abe, J. Phys. Chem. B 1999, 103, 10737-10740.
33. T. Hamada, Y. T. Sato, K. Yoshikawa, T. Nagasaki, Langmuir 2005, 21, 7626-7628.
34. F. M. Mansfeld, G. Q. Feng, S. Otto, Org. Biomol. Chem. 2009, 7, 4289-4295.
35. Y. P. Wang, P. Han, H. P. Xu, Z. Q. Wang, X. Zhang, A. V. Kabanov, Langmuir 2010, 26, 709-715.
36. A. Ueno, H. Yoshimura, R. Saka, T. Osa, J. Am. Chem. Soc. 1979, 101, 2779-2780.
37. A. Ueno, Y. Tomita, T. Osa, Tetrahedron Lett. 1983, 24, 5245-5248.
38. I. Tomatsu, A. Hashidzume, A. Harada, Macromolecules 2005, 38, 5223-5227.
39. I. Tomatsu, A. Hashidzume, A. Harada, J. Am. Chem. Soc. 2006, 128, 2226-2227.
40. G. Pouliquen, C. Amiel, C. Tribet, J. Phys. Chem. B 2007, 111, 5587-5595.
41. Y. L. Zhao, J. F. Stoddart, Langmuir 2009, 25, 8442-8446.
42. X. Liao, G. Chen, X. Liu, W. Chen, F. Chen, M. Jiang, Angew. Chem. 2010, 122, 4511-4515
43. Angew. Chem. Int. Ed. 2010, 49, 4409-4413.
44. S. Tamesue, Y. Takashima, H. Yamaguchi, S. Shinkai, A. Harada, Angew. Chem. 2010, 122, 7623-7626
45. Angew. Chem. Int. Ed. 2010, 49, 7461-7464.
46. J. Liu, G. Chen, M. Guo, M. Jiang, Macromolecules 2010, 43, 8086-8093.
47. K. Peng, I. Tomatsu, A. Kros, Chem. Commun. 2010, 46, 4094-4096.
48. H. Murakami, A. Kawabuchi, K. Kotoo, M. Kunitake, N. Nakashima, J. Am. Chem. Soc. 1997, 119, 7605-7606.
49. G. Wenz, B. H. Han, A. Müller, Chem. Rev. 2006, 106, 782-817.
50. Y. P. Wang, N. Ma, Z. Q. Wang, X. Zhang, Angew. Chem. 2007, 119, 2881-2884
51. Angew. Chem. Int. Ed. 2007, 46, 2823-2826.
52. X. Chen, L. Hong, X. You, Y. L. Wang, G. Zou, W. Su, Q. J. Zhang, Chem. Commun. 2009, 1356-1358.
53. J. Zou, B. Guan, X. J. Liao, M. Jiang, F. G. Tao, Macromolecules 2009, 42, 7465-7473.
54. Y. P. Wang, M. Zhang, C. Moers, S. L. Chen, H. P. Xu, Z. Q. Wang, X. Zhang, Z. B. Li, Polymer 2009, 50, 4821-4828.
55. P. V. Jog, M. S. Gin, Org. Lett. 2008, 10, 3693-3696.
56. A. Yabe, Y. Kawabata, H. Niino, M. Tanaka, A. Ouchi, H. Takahashi, S. Tamura, W. Tagaki, H. Nakahara, K. Fukuda, Chem. Lett. 1988, 1-4.
57. P. B. Wan, Y. G. Jiang, Y. P. Wang, Z. Q. Wang, X. Zhang, Chem. Commun. 2008, 5710-5712.
58. D. P. Ferris, Y. L. Zhao, N. M. Khashab, H. A. Khatib, J. F. Stoddart, J. I. Zink, J. Am. Chem. Soc. 2009, 131, 1686-1688.
59. B. J. Ravoo, R. Darcy, Angew. Chem. 2000, 112, 4494-4496
60. Angew. Chem. Int. Ed. 2000, 39, 4324-4326.
61. A. Mazzaglia, R. Donohue, B. J. Ravoo, R. Darcy, Eur. J. Org. Chem. 2001, 1715-1721.
62. B. J. Ravoo, J. C. Jacquier, G. Wenz, Angew. Chem. 2003, 115, 2112-2116
63. Angew. Chem. Int. Ed. 2003, 42, 2066-2070.
64. P. Falvey, C. W. Lim, R. Darcy, T. Revermann, U. Karst, M. Giesbers, A. T. M. Marcelis, A. Lazar, A. W. Coleman, D. N. Reinhoudt, B. J. Ravoo, Chem. Eur. J. 2005, 11, 1171-1180.
65. C. W. Lim, B. J. Ravoo, D. N. Reinhoudt, Chem. Commun. 2005, 5627-5629.
66. C. W. Lim, O. Crespo-Biel, M. C. A. Stuart, D. N. Reinhoudt, J. Huskens, B. J. Ravoo, Proc. Natl. Acad. Sci. USA 2007, 104, 6986-6991.
67. F. Versluis, I. Tomatsu, S. Kehr, C. Fregonese, A. W. J. W. Tepper, M. C. A. Stuart, B. J. Ravoo, R. I. Koning, A. Kros, J. Am. Chem. Soc. 2009, 131, 13186-13187.
68. J. Voskuhl, M. C. A. Stuart, B. J. Ravoo, Chem. Eur. J. 2010, 16, 2790-2796.
69. J. Voskuhl, T. Fenske, M. Stuart, B. Wibbeling, C. Schmuck, B. J. Ravoo, Chem. Eur. J. 2010, 16, 8300-8306.
70. R. V. Vico, J. Voskuhl, B. J. Ravoo, Langmuir 2011, 27, 1391-1397.
71. For a short review, see:, J. Voskuhl, B. J. Ravoo, Chem. Soc. Rev. 2009, 38, 495-505.
72. S. K. M. Nalluri, B. J. Ravoo, Angew. Chem. 2010, 122, 5499-5502
73. Angew. Chem. Int. Ed. 2010, 49, 5371-5374.
74. M. V. Rekharsky, Y. Inoue, Chem. Rev. 1998, 98, 1875-1917.
75. S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1998, 98, 1959-1976.
76. A. Harada, Acc. Chem. Res. 2001, 34, 456-464.
77. J. Szejtli, Chem. Rev. 1998, 98, 1743-1754.