Environmentally responsive threading, dethreading, and fixation of anion-induced pseudorotaxanes

Journal of the American Chemical Society

Volumn 133, Issue 5, 2011, Pages 1526-1533

  Gong, Han Yuan ^a   Rambo, Brett M ^a   Karnas, Elizabeth ^a   Lynch, Vincent M ^a   Keller, Karin M ^a   Sessler, Jonathan L ^a,b  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b Yonsei University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ENVIRONMENTAL STIMULI; EXTENDED STRUCTURES; HEXAFLUOROPHOSPHATES; IMIDAZOL; MACROCYCLES; NMR SPECTROSCOPY; POLYROTAXANES; PSEUDOROTAXANES; SINGLE CRYSTAL X-RAY DIFFRACTION;

CARBOXYLATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILVER COMPOUNDS; X RAY DIFFRACTION;

HYDROGELS;

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; ANION; CARBOXYLIC ACID DERIVATIVE; PSEUDOROTAXANE; ROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENVIRONMENTAL FACTOR; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PH; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; TEMPERATURE; X RAY DIFFRACTION;

EID: 79551699534     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109102k     Document Type: Article

References (54)

1. Lehn, J. M. Science 1985, 227, 849-856
2. Lehn, J. M. Angew. Chem. 1990, 102, 1347-1362
3. Lehn, J. M. Science 1993, 260, 1762-1763
4. Lankshear, M. D.; Beer, P. D. Acc. Chem. Res. 2007, 40, 657-668
5. Beer, P. D.; Sambrook, M. R.; Curiel, D. Chem. Commun. 2006, 2105-2117
6. Chmielewski, M. J.; Zhao, L.; Brown, A.; Curiel, D.; Sambrook, M. R.; Thompson, A. L.; Santos, S. M.; Felix, V.; Davis, J. J.; Beer, P. D. Chem. Commun. 2008, 3154-3156
7. Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828
8. Schalley, C. A.; Weilandt, T.; Brüggemann, J.; Vögtle, F. Top. Curr. Chem. 2004, 248, 141-200
9. Gassensmith, J. J.; Baumes, J. M.; Smith, B. D. Chem. Commun. 2009, 6329-6338
10. Schill, G. Catenanes, Rotaxanes, and Knots; Academic Press: San Diego, CA, 1971.
11. Dietrich-Buchecker, C.; Sauvage, J. P. Chem. Rev. 1987, 87, 795-810
12. Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P.; Dietrich-Buchecker, C. O., Eds.; Wiley-VCH: Weinheim, 1999.
13. Collin, J.-P.; Heitz, V.; Sauvage, J.-P. Top. Curr. Chem. 2005, 262, 26-62
14. Niu, Z.; Gibson, H. W. Chem. Rev. 2009, 109, 6024-6046
15. Fujita, M. Acc. Chem. Res. 1999, 32, 53-61
16. Mason, P. E.; Parsons, I. W.; Tolley, M. S. Angew. Chem., Int. Ed. 1996, 35, 2238-2241
17. Huang, F.; Gibson, H. W. Prog. Polym. Sci. 2005, 30, 982-1018
18. Wenz, G.; Han, B.-H.; Mueller, A. Chem. Rev. 2006, 106, 782-817
19. Fang, L.; Olson, M. A.; Benitez, D.; Tkatchouk, E.; Goddard, W. A., III; Stoddart, J. F. Chem. Soc. Rev. 2010, 39, 17-29
20. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Chem. Rev. 2009, 109, 5974-6023
21. Shen, Y. X.; Xie, D.; Gibson, H. W. J. Am. Chem. Soc. 1994, 116, 537-548
22. Takata, T.; Kihara, N.; Furusho, Y. Adv. Polym. Sci. 2004, 171, 1-75
23. Mullen, K. M.; Beer, P. D. Chem. Soc. Rev. 2009, 38, 1701-1713
24. Mullen, K. M.; Mercurio, J.; Serpell, C. J.; Beer, P. D. Angew. Chem., Int. Ed. 2009, 48, 4781-4784
25. Chmielewski, M. H.; Zhao, L.; Brown, A.; Curiel, D.; Sambrook, M. R.; Thompson, A. L.; Santos, S. M.; Felix, V.; Davis, J. J.; Beer, P. D. Chem. Commun. 2008, 3154-3156
26. Hoffart, D. J.; Tiburcio, J.; de la Torre, A.; Knight, L. K.; Loeb, S. J. Angew. Chem., Int. Ed. 2008, 47, 97-101
27. Lestini, E.; Nikitin, K.; Mueller-Bunz, H.; Fitzmaurice, D. Chem.-Eur. J. 2008, 14, 1095-1106
28. Knight, L. K.; Vukotic, V. N.; Viljoen, E.; Caputo, C. B.; Loeb, S. J. Chem. Commun. 2009, 5585-5587
29. Gong, H.-Y.; Rambo, B. M.; Karnas, E.; Lynch, V. M.; Sessler, J. L. Nat. Chem. 2010, 2, 406-409
30. Murray, L. J.; Dincǎ, M.; Long, J. R. Chem. Soc. Rev. 2009, 38, 1294-1314
31. Balzani, V.; Gómez-López, M.; Stoddart, J. F. Acc. Chem. Res. 1998, 31, 405-414
32. Pease, A. R.; Jeppesen, J. O.; Stoddart, J. F.; Luo, Y.; Collier, C. P.; Heath, J. R. Acc. Chem. Res. 2001, 34, 433-444
33. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191
34. Bissell, R. A.; Córdova, E.; Kaifer, R. A.; Stodart, J. F. Nature (London) 1994, 369, 133-137
35. Stoddart, J. F. Chem. Soc. Rev. 2009, 38, 1521-1529
36. Crowley, J. D.; Goldup, S. M.; Lee, A.-L.; Leigh, D. A Chem. Soc. Rev. 2009, 38, 1530-1541
37. Deng, H.; Olson, M. A.; Stoddart, J. F.; Yaghi, O. Nat. Chem. 2010, 2, 439-443
38. Long, J. R.; Yaghi, O. M. Chem. Soc. Rev. 2009, 38, 1213-1214
39. Li, Q.; Zhang, W.; Milajaní, O. Š.; Sue, C.-H.; Zhao, Y.-L.; Liu, L.; Knobler, C. B.; Stoddart, J. F.; Yaghi, O. M. Science 2009, 325, 855-859
40. Li, Q.; Zhang, W.; Milajaní, O. Š.; Knobler, C. B.; Stoddart, J. F.; Yaghi, O. M. Chem. Commun. 2010, 46, 380-382
41. Zhao, Y.-L.; Liu, L.; Zhang, W.; Sue, C.-H.; Li, Q.; Milanaí, O. Š.; Yaghi, O. M.; Stoddart, J. F. Chem.-Eur. J. 2009, 15, 1356-13380
42. Park, K.-M.; Kim, S.-Y.; Heo, J.; Whang, D.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2002, 124, 2140-2147
43. Kim, K. Chem. Soc. Rev. 2002, 31, 96-107
44. Liu, Y.; Wang, H.; Zhang, H.-Y.; Liang, P. Chem. Commun. 2004, 2266-2267
45. Liu, Y.; Zhao, Y.-L.; Zhang, H.-Y.; Song, H.-B. Angew. Chem., Int. Ed. 2003, 42, 3260-3263
46. Liu, Y.; Song, S.-H.; Chen, Y.; Zhao, Y.-L.; Yang, Y.-W. Chem. Commun. 2005, 170, 2-1704
47. Loeb, S. J. Chem. Soc. Rev. 2007, 36, 226-235
48. Davidson, G. J. E.; Loeb, S. J. Angew. Chem., Int. Ed. 2003, 42, 74-77
49. Hoffart, D. J.; Loeb, S. J. Angew. Chem., Int. Ed. 2005, 44, 901-944
50. Pang, H.-J.; Peng, J.; Zhang, C.-J.; Li, Y.-G.; Zhang, P.-P.; Ma, H.-Y.; Su, Z.-M. Chem. Commun. 2010, 46, 5097-5099
51. Wang, X.-L.; Qin, C.; Wang, E.-B.; Su, Z.-M. Chem. Commun. 2007, 4245-4247
52. - counteranions.
53. It is observed that the supramolecular dimeric species have different charges in solution than they do in the gas phase; this is thought to reflect the formation of various cation radicals under the conditions of mass spectrometric analysis as the result of proton-transfer processes.
54. Sun, D.; Zhang, N.; Xu, Q.-J.; Huang, R.-B.; Zheng, L.-S. J. Organomet. Chem. 2010, 695, 1598-1602 Interestingly, the 2:1 carboxylate-to-Ag(I) coordination mode differs from the 2:2 complexation generally seen in simple (i.e., non-interpenetrated) polymers built up from dicarboxylate dianions and Ag(I) cations; cf., e.g.