Light-triggered guest uptake and release by a photochromic coordination cage

Angewandte Chemie - International Edition

Volumn 52, Issue 4, 2013, Pages 1319-1323

  Han, Muxin ^a   Michel, Reent ^a   He, Bice ^a   Chen, Yu Sheng ^b   Stalke, Dietmar ^a   John, Michael ^a   Clever, Guido H ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

anion recognition; cage compounds; host guest systems; photoswitches; supramolecular chemistry

Indexed keywords

ANION RECOGNITION; CAGE COMPOUNDS; COORDINATION CAGE; DITHIENYLETHENE; HOST-GUEST SYSTEM; INTERCONVERSIONS; PHOTOSWITCHES; SELF-ASSEMBLED;

SUPRAMOLECULAR CHEMISTRY;

PHOTOCHROMISM;

EID: 84872377614     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201207373     Document Type: Article

References (96)

1. A. Rajbanshi, B. A. Moyer, R. Custelcean, Cryst. Growth Des. 2011, 11, 2702
2. W. Meng, B. Breiner, K. Rissanen, J. D. Thoburn, J. K. Clegg, J. R. Nitschke, Angew. Chem. 2011, 123, 3541
3. Angew. Chem. Int. Ed. 2011, 50, 3479.
4. P. Mal, B. Breiner, K. Rissanen, J. R. Nitschke, Science 2009, 324, 1697
5. I. A. Riddell, M. M. J. Smulders, J. K. Clegg, J. R. Nitschke, Chem. Commun. 2011, 47, 457.
6. D. Cram, M. Tanner, R. Thomas, Angew. Chem. 1991, 103, 1048
7. Angew. Chem. Int. Ed. Engl. 1991, 30, 1024
8. K. Goto, R. Okazaki, Liebigs Ann./Recueil 1997, 2393
9. M. Ziegler, J. Brumaghim, K. Raymond, Angew. Chem. 2000, 112, 4285
10. Angew. Chem. Int. Ed. 2000, 39, 4119
11. D. Fiedler, R. G. Bergman, K. N. Raymond, Angew. Chem. 2006, 118, 759
12. Angew. Chem. Int. Ed. 2006, 45, 745
13. M. Kawano, Y. Kobayashi, T. Ozeki, M. Fujita, J. Am. Chem. Soc. 2006, 128, 6558
14. F. Hapiot, S. Tilloy, E. Monflier, Chem. Rev. 2006, 106, 767
15. T. Iwasawa, R. J. Hooley, J. Rebek, Science 2007, 317, 493
16. R. J. Hooley, J. Rebek, Chem. Biol. 2009, 16, 255
17. C.-Y. Gao, L. Zhao, M.-X. Wang, J. Am. Chem. Soc. 2012, 134, 824.
18. J. L. Sessler, P. Gale, W.-S. Cho, S. J. Rowan, Anion Receptor Chemistry (Monographs in Supramolecular Chemistry), Royal Society of Chemistry, London, 2006
19. R. Custelcean, J. Bosano, P. V. Bonnesen, V. Kertesz, B. P. Hay, Angew. Chem. 2009, 121, 4085
20. Angew. Chem. Int. Ed. 2009, 48, 4025
21. S. O. Kang, J. M. Llinares, V. W. Day, K. Bowman-James, Chem. Soc. Rev. 2010, 39, 3980
22. M. Wang, V. Vajpayee, S. Shanmugaraju, Y.-R. Zheng, Z. Zhao, H. Kim, P. S. Mukherjee, K.-W. Chi, P. J. Stang, Inorg. Chem. 2011, 50, 1506
23. J. A. Thomas, Dalton Trans. 2011, 40, 12005.
24. T. D. Nguyen, Y. Liu, S. Saha, K. C. F. Leung, J. F. Stoddart, J. I. Zink, J. Am. Chem. Soc. 2007, 129, 626
25. P. Mal, D. Schultz, K. Beyeh, K. Rissanen, J. R. Nitschke, Angew. Chem. 2008, 120, 8421
26. Angew. Chem. Int. Ed. 2008, 47, 8297
27. F. Schmitt, J. Freudenreich, N. P. E. Barry, L. Juillerat-Jeanneret, G. Süss-Fink, B. Therrien, J. Am. Chem. Soc. 2012, 134, 754
28. Z. Ma, B. Moulton, Coord. Chem. Rev. 2011, 255, 1623
29. J. E. M. Lewis, E. L. Gavey, S. A. Cameron, J. D. Crowley, Chem. Sci. 2012, 3, 778.
30. D. Vriezema, M. Aragones, J. Elemans, J. Cornelissen, A. Rowan, R. Nolte, Chem. Rev. 2005, 105, 1445
31. M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. 2009, 121, 3470
32. Angew. Chem. Int. Ed. 2009, 48, 3418
33. Molecular Encapsulation: Organic Reactions in Constrained Systems (Eds.:, U. H. Brinker, J. Mieusset,), Wiley, Hoboken, 2010
34. M. J. Wiester, P. A. Ulmann, C. A. Mirkin, Angew. Chem. 2011, 123, 118
35. Angew. Chem. Int. Ed. 2011, 50, 114.
36. D. Fiedler, H. van Halbeek, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc. 2006, 128, 10240
37. C. J. Hastings, M. D. Pluth, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc. 2010, 132, 6938.
38. D. Sud, T. B. Norsten, N. R. Branda, Angew. Chem. 2005, 117, 2055
39. Angew. Chem. Int. Ed. 2005, 44, 2019
40. R. S. Stoll, S. Hecht, Angew. Chem. 2010, 122, 5176
41. Angew. Chem. Int. Ed. 2010, 49, 5054
42. J. Wang, B. L. Feringa, Science 2011, 331, 1429
43. U. Lüning, Angew. Chem. 2012, 124, 8285
44. Angew. Chem. Int. Ed. 2012, 51, 8163.
45. G. H. Clever, S. Tashiro, M. Shionoya, J. Am. Chem. Soc. 2010, 132, 9973.
46. H. Dube, D. Ajami, J. Rebek, Angew. Chem. 2010, 122, 3260
47. Angew. Chem. Int. Ed. 2010, 49, 3192
48. H. Dube, J. Rebek, Angew. Chem. 2012, 124, 3261
49. Angew. Chem. Int. Ed. 2012, 51, 3207.
50. The blocking of voltage-gated ion channels by light-switchable binders is comparable to encapsulation processes in artificial cages:, M. R. Banghart, A. Mourot, D. L. Fortin, J. Z. Yao, R. H. Kramer, D. Trauner, Angew. Chem. 2009, 121, 9261
51. Angew. Chem. Int. Ed. 2009, 48, 9097.
52. G. H. Clever, in Molecules at Work (Ed.:, B. Pignataro,), Wiley-VCH, Weinheim, 2012.
53. M. Irie, M. Kato, J. Am. Chem. Soc. 1985, 107, 1024.
54. S. Shinkai, M. Ishihara, K. Ueda, O. Manabe, J. Incl. Phenom. 1984, 2, 111.
55. M. Blank, L. Soo, N. Wassermann, B. Erlanger, Science 1981, 214, 70.
56. R. Rojanathanes, T. Tuntulani, W. Bhanthumnavin, M. Sukwattanasinitt, Org. Lett. 2005, 7, 3401.
57. A. Ueno, H. Yoshimura, R. Saka, T. Osa, J. Am. Chem. Soc. 1979, 101, 2779.
58. R. Reuter, N. Hostettler, M. Neuburger, H. Wegner, Eur. J. Org. Chem. 2009, 5647
59. N. Iwasawa, H. Takahagi, K. Ono, K. Fujii, H. Uekusa, Chem. Commun. 2012, 48, 7477
60. S. Chen, L.-J. Chen, H.-B. Yang, H. Tian, W. Zhu, J. Am. Chem. Soc. 2012, 134, 13596.
61. H. Kai, S. Nara, K. Kinbara, T. Aida, J. Am. Chem. Soc. 2008, 130, 6725.
62. Covalently attached azobenzenes were used for switching the interior hydrophobicity (but not structure) of a coordination cage:, T. Murase, S. Sato, M. Fujita, Angew. Chem. 2007, 119, 5225
63. Angew. Chem. Int. Ed. 2007, 46, 5133.
64. M. Fujita, K. Umemoto, M. Yoshizawa, N. Fujita, T. Kusukawa, K. Biradha, Chem. Commun. 2001, 509
65. S. J. Dalgarno, N. P. Power, J. L. Atwood, Coord. Chem. Rev. 2008, 252, 825
66. D. Tranchemontagne, Z. Ni, M. O'Keeffe, O. Yaghi, Angew. Chem. 2008, 120, 5214
67. Angew. Chem. Int. Ed. 2008, 47, 5136.
68. D. A. McMorran, P. J. Steel, Angew. Chem. 1998, 110, 3495
69. Angew. Chem. Int. Ed. 1998, 37, 3295
70. D. K. Chand, K. Biradha, M. Fujita, Chem. Commun. 2001, 1652
71. C. Su, Y. P. Cai, C. Chen, M. D. Smith, W. Kaim, H. C. zur Loye, J. Am. Chem. Soc. 2003, 125, 8595
72. N. L. S. Yue, D. J. Eisler, M. C. Jennings, R. J. Puddephatt, Inorg. Chem. 2004, 43, 7671
73. G. H. Clever, S. Tashiro, M. Shionoya, Angew. Chem. 2009, 121, 7144
74. Angew. Chem. Int. Ed. 2009, 48, 7010
75. P. Liao, B. W. Langloss, A. M. Johnson, E. R. Knudsen, F. S. Tham, R. R. Julian, R. J. Hooley, Chem. Commun. 2010, 46, 4932
76. N. Kishi, Z. Li, K. Yoza, M. Akita, M. Yoshizawa, J. Am. Chem. Soc. 2011, 133, 11438
77. G. H. Clever, W. Kawamura, S. Tashiro, M. Shiro, M. Shionoya, Angew. Chem. 2012, 124, 2660
78. Angew. Chem. Int. Ed. 2012, 51, 2606
79. S. Freye, J. Hey, A. Torras Galán, D. Stalke, R. Herbst Irmer, M. John, G. H. Clever, Angew. Chem. 2012, 124, 2233
80. Angew. Chem. Int. Ed. 2012, 51, 2191
81. D. M. Engelhard, S. Freye, K. Grohe, M. John, G. H. Clever, Angew. Chem. 2012, 124, 4828
82. Angew. Chem. Int. Ed. 2012, 51, 4747.
83. M. Irie, Chem. Rev. 2000, 100, 1685.
84. S. Fraysse, C. Coudret, J. P. Launay, Eur. J. Inorg. Chem. 2000, 1581
85. B. He, O. S. Wenger, J. Am. Chem. Soc. 2011, 133, 17027.
86. Y. Ishibashi, M. Fujiwara, T. Umesato, H. Saito, S. Kobatake, M. Irie, H. Miyasaka, J. Phys. Chem. C 2011, 115, 4265.
87. G. H. Clever, M. Shionoya, Chem. Eur. J. 2010, 16, 11792.
88. T. Weilandt, U. Kiehne, J. Bunzen, G. Schnakenburg, A. Lützen, Chem. Eur. J. 2010, 16, 2418
89. N. Ousaka, J. K. Clegg, J. R. Nitschke, Angew. Chem. 2012, 124, 1493
90. Angew. Chem. Int. Ed. 2012, 51, 1464.
91. M. Han, J. Hey, W. Kawamura, D. Stalke, M. Shionoya, G. H. Clever, Inorg. Chem. 2012, 51, 9574.
92. G. H. Clever, W. Kawamura, M. Shionoya, Inorg. Chem. 2011, 50, 4689.
93. P. Thordarson, Chem. Soc. Rev. 2011, 40, 1305.
94. R. F. Barth, J. A. Coderre, M. Vicente, T. E. Blue, Clin. Cancer Res. 2005, 11, 3987.
95. E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72
96. Angew. Chem. Int. Ed. 2007, 46, 72.