Inclusion complexation of diquat and paraquat by the hosts cucurbit [7] uril and cucurbit [8] uril

Chemistry - A European Journal

Volumn 13, Issue 28, 2007, Pages 7908-7914

  Ling, Yonghua ^a   Mague, Joel T ^b   Kaifer, Angel E ^a  

^a University of Miami   (United States)

^b Tulane University   (United States)

Author keywords

Cyclic voltammetry; Electrochemistry; Host guest systems; Inclusion compounds; Supramolecular chemistry

Indexed keywords

BINDING AFFINITY; HOST-GUEST SYSTEMS; INCLUSION COMPOUNDS; ONE-ELECTRON REDUCTION;

CHARGE DISTRIBUTION; CYCLIC VOLTAMMETRY; DIMERS; ELECTROCHEMISTRY; FLUORESCENCE SPECTROSCOPY; MASS SPECTROMETRY; SUPRAMOLECULAR CHEMISTRY;

COMPLEXATION;

BRIDGED COMPOUND; CUCURBIT(7)URIL; CUCURBIT(8)URIL; DIQUAT; IMIDAZOLE DERIVATIVE; PARAQUAT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY; X RAY DIFFRACTION;

BRIDGED COMPOUNDS; DIQUAT; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; PARAQUAT; SOLUTIONS; WATER; X-RAY DIFFRACTION;

EID: 35048835731     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700402     Document Type: Article

References (45)

1. P. Monk, The Viologens: Physicochemical Properties, Synthesis and Applications of the Salts of 4,4′-Bipyridine, Wiley, New York, 1998, Chapter 5.
2. J. W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, K. Kim, Acc. Chem. Res. 2003, 36, 621.
3. J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. Isaacs, Angew. Chem. 2005, 117, 4922;
4. Angew. Chem. Int. Ed. 2005, 44, 4844.
5. 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.
6. H.-J. Kim, W. S. Jeon, Y. H. Ko, K. Kim, Proc. Natl. Acad. Sci. USA 2002, 99, 5007.
7. W. Ong, M. Gomez-Kaifer, A. E. Kaifer, Org. Lett. 2002, 4, 1791.
8. Y. J. Jeon, H.-J. Kim, C. Lee, K. Kim. Chem. Commun. 2002, 1828.
9. H.-J. Kim, J. Heo, W. S. Jeon, E. Lee, J. Kim, S. Sakamoto, K. Yamaguchi, K. Kim, Angew. Chem. 2001, 113, 1574;
10. Angew. Chem. Int. Ed. 2001, 40, 1526.
11. W. S. Jeon, P. K. Bharadwaj, S. W. Choi, J. W. Lee, K. Kim, Angew. Chem. 2002, 114, 4654;
12. Angew. Chem. Int. Ed. 2002, 41, 4474.
13. J. W. Lee, K. Kim, S. W. Choi, Y. H. Ko, S. Sakamoto, K. Yamaguchi, K. Kim, Chem. Commun. 2002, 2692.
14. W. S. Jeon, A. Y. Ziganshina, Y. H. Ko, J.-K. Kang, J. W. Lee, C. Lee, K. Kim, Angew. Chem. 2003, 115, 4231;
15. Angew. Chem. Int. Ed. 2003, 42, 4097.
16. K. Kim, D. Kim, J. W. Lee, Y. H. Ko, K. Kim, Chem. Commun. 2004, 848.
17. Y. H. Ko, K. Kim, J.-K. Kang, H. Chun, J. W. Lee, S. Sakamoto, K. Yamaguchi, J. C. Fettinger, K. Kim, J. Am. Chem. Soc. 2004, 126, 1932.
18. W. S. Jeon, E. Kim, Y. H. Ko, I. Hwang, J. W. Lee, S.-Y. Kim, H.-J. Kim, K. Kim, Angew. Chem. 2005, 117, 89;
19. Angew. Chem. Int. Ed. 2005, 44, 87.
20. Y. H. Ko, Eunju Kim, I. Hwang, K. Kim, Chem. Commun. 2007, 1305.
21. K. Moon, J. Grindstaff, D. Sobransingh, A. E. Kaifer, Angew. Chem. 2004, 176, 5612;
22. Angew. Chem. Int. Ed. 2004, 43, 5496.
23. W. Wang, A. E. Kaifer, Angew. Chem. 2006, 118, 7200;
24. Angew. Chem. Int. Ed. 2006, 45, 7042.
25. V. Sindelar, M. A. Cejas, F. M. Raymo, A. E. Kaifer, New J. Chem. 2005, 29, 280.
26. Y. Ling, W. Wang, A. E. Kaifer, Chem. Commun. 2007, 610.
27. V. Sindelar, M. A. Cejas, F. M. Raymo, W. Chen, S. E. Parker, A. E. Kaifer, Chem. Eur. J. 2005, 11, 7054.
28. See, for instance: W. Ong, A. E. Kaifer, J. Org. Chem. 2004, 69, 1383.
29. T. Pérez-Ruiz, C. Martínez-Lozano, V. Tomás, J. Fenoll, Analyst 2000, 125, 2372.
30. A. E. Kaifer, M. Gómez-Kaifer, Supramolecular Electrochemistry, Wiley-VCH, Weinheim, 1999, Chapter 9.
31. The program used for digital simulations was DigiElch v2.0. The program was used under permission from ElchSoft. References [25-29] provide theoretical background for the simulation program.
32. M. Rudolph, J. Electroanal. Chem. 2003, 543, 23.
33. M. Rudolph, J. Electroanal. Chem. 2004, 571, 289.
34. M. Rudolph, J. Comput. Chem. 2005, 26, 619.
35. M. Rudolph, J. Comput. Chem. 2005, 26, 633.
36. M. Rudolph, J. Comput. Chem. 2005, 26, 1193.
37. T. Matsue, D. H. Evans, T. Osa, N. Kobayashi, J. Am. Chem. Soc. 1985, 107, 3411.
38. R. Isnin, C. Salam, A. E. Kaifer, J. Org. Chem. 1991, 56, 35.
39. Y. Wang, S. Mendoza, A. E. Kaifer, Inorg. Chem. 1998, 37, 317.
40. Y. Cohen, L. Avram, L. Frish, Angew. Chem. 2005, 117, 524;
41. Angew. Chem. Int. Ed. 2005, 44, 520.
42. P. S. Braterman, J.-I. Song, J. Org. Chem. 1991, 56, 4678.
43. E. F. Bowden, F. M. Hawkridge. J. Electroanal. Chem. Interfacial Electrochem. 1981, 125, 367.
44. J. E. Dickeson, L. A. Summers, Experientia 1969, 25, 1274.
45. A. Day, A. P. Arnold, R. J. Blanch, B. Snushall, J. Org. Chem. 2001, 66, 8094.