Controlled molecular self-assembly behaviors between cucurbituril and bispyridinium derivatives

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4682-4685

  Zhang, Zhi Jun ^a   Zhang, Ying Ming ^a   Liu, Yu ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

[2]PSEUDOROTAXANES; ACIDIC CONDITIONS; CUCURBITURILS; INTERCONVERSIONS; MOLECULAR SELF ASSEMBLY; SPECTROSCOPIC BEHAVIOR;

MOLECULAR BIOLOGY;

MOLECULAR RECOGNITION;

CHEMICAL COMPOUND; CUCURBIT[8]URIL; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SUPRAMOLECULAR CHEMISTRY;

EID: 79957832227     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200349u     Document Type: Article

References (35)

1. Balzani, V.; Credi, A.; Venturi, M. Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld, 2 nd ed.; Wiley-VCH: Weinheim, 2008.
2. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72
3. Tian, H.; Wang, Q. C. Chem. Soc. Rev. 2006, 35, 361
4. Saha, S.; Stoddart, J. F. Chem. Soc. Rev. 2007, 36, 77
5. Leung, K. C. F.; Chak, C. P.; Lo, C. M.; Wong, W. Y.; Xuan, S.; Cheng, C. H. K. Chem.-Asian J. 2009, 4, 364
6. Zhang, H.; Wang, Q.; Liu, M.; Ma, X.; Tian, H. Org. Lett. 2009, 11, 3234
7. Inoue, Y.; Kuad, P.; Okumura, Y.; Takashima, Y.; Yamaguchi, H.; Harada, A. J. Am. Chem. Soc. 2007, 129, 6396
8. Qu, D. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2010, 49, 1107
9. Sharma, S.; Davidson, G. J.; Loeb, S. J. Chem. Commun. 2008, 582
10. Chuang, C. J.; Li, W. S.; Lai, C. C.; Liu, Y. H.; Peng, S. M.; Chao, I.; Chiu, S. H. Org. Lett. 2009, 11, 385
11. Busseron, E.; Romuald, C.; Coutrot, F. Chem.-Eur. J. 2010, 16, 10062
12. Collin, J. P.; Frey, J.; Heitz, V.; Sauvage, J. P.; Tock, C.; Allouche, L. J. Am. Chem. Soc. 2009, 131, 5609
13. Davidson, G. J.; Sharma, S.; Loeb, S. J. Angew. Chem., Int. Ed. 2010, 49, 4938
14. Loeb, S. J.; Tiburcio, J.; Vella, S. J. Chem. Commun. 2006, 1598
15. Spruell, J. M.; Paxton, W. F.; Olsen, J. C.; Benitez, D.; Tkatchouk, E.; Stern, C. L.; Trabolsi, A.; Friedman, D. C.; Goddard, W. A., III; Stoddart, J. F. J. Am. Chem. Soc. 2009, 131, 11571
16. Yu, Z.; Hecht, S. Angew. Chem., Int. Ed. 2011, 50, 1640
17. de Las Heras Alarcon, C.; Pennadam, S.; Alexander, C. Chem. Soc. Rev. 2005, 34, 276
18. Zhang, X.; Wang, C. Chem. Soc. Rev. 2011, 40, 94
19. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844
20. Ko, Y. H.; Kim, E.; Hwang, I.; Kim, K. Chem. Commun. 2007, 1305
21. Hwang, I.; Ziganshina, A. Y.; Ko, Y. H.; Yun, G.; Kim, K. Chem. Commun. 2009, 416
22. Jeon, W. S.; Kim, E.; Ko, Y. H.; Hwang, I.; Lee, J. W.; Kim, S. Y.; Kim, H. J.; Kim, K. Angew. Chem., Int. Ed. 2004, 44, 87
23. Lee, J. W.; Hwang, I.; Jeon, W. S.; Ko, Y. H.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Chem.-Asian J. 2008, 3, 1277
24. Yang, C.; Ko, Y. H.; Selvapalam, N.; Origane, Y.; Mori, T.; Wada, T.; Kim, K.; Inoue, Y. Org. Lett. 2007, 9, 4789
25. Jeon, W. S.; Ziganshina, A. Y.; Lee, J. W.; Ko, Y. H.; Kang, J. K.; Lee, C.; Kim, K. Angew. Chem., Int. Ed. 2003, 42, 4097
26. For more detailed discussion, sees Figure S15 and S16, Supporting Information.
27. Cohen, Y.; Avram, L.; Frish, L. Angew. Chem., Int. Ed. 2005, 44, 520
28. Wang, F.; Zhang, J.; Ding, X.; Dong, S.; Liu, M.; Zheng, B.; Li, S.; Wu, L.; Yu, Y.; Gibson, H. W.; Huang, F. Angew. Chem., Int. Ed. 2010, 49, 1090
29. Lee, J. W.; Kim, K.; Choi, S.; Ko, Y. H.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Chem. Commun. 2002, 2692
30. Guo, J. B.; Jiang, Y.; Chen, C. F. Org. Lett. 2010, 12, 5764
31. Tomimasu, N.; Kanaya, A.; Takashima, Y.; Yamaguchi, H.; Harada, A. J. Am. Chem. Soc. 2009, 131, 12339
32. If there was a 2:2 complex or n: n polymeric species in the aqueous solution, there should be more than one species in the DOSY spectra and the size of the complex formed by 3 and CB[8] should be more than 2 times larger than the one of free CB[8]. See Figure S21 in the Supporting Information for the possible structure of the 2:2 complex and n: n polymeric species.
33. Baek, K.; Kim, Y.; Kim, H.; Yoon, M.; Hwang, I.; Ko, Y. H.; Kim, K. Chem. Commun. 2010, 4091
34. Rekharsky, M. V.; Mori, T.; Yang, C.; Ko, Y. H.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A. E.; Liu, S.; Isaacs, L.; Chen, W.; Moghaddam, S.; Gilson, M. K.; Kim, K.; Inoue, Y. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 20737
35. Liu, Y.; Li, X. Y.; Zhang, H. Y.; Li, C. J.; Ding, F. J. Org. Chem. 2007, 72, 3640