Reconfigurable four-component molecular switch based on pH-controlled guest swapping

Organic Letters

Volumn 9, Issue 12, 2007, Pages 2349-2352

  Chakrabarti, Sriparna ^a   Mukhopadhyay, Pritam ^a   Lin, Shirley ^b   Isaacs, Lyle ^a  

^a Bldg 142   (United States)

^b UNITED STATES NAVAL ACADEMY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; BRIDGED COMPOUND; CUCURBIT(6)URIL; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; SENSITIVITY AND SPECIFICITY;

BETA-CYCLODEXTRINS; BRIDGED COMPOUNDS; HYDROGEN-ION CONCENTRATION; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SENSITIVITY AND SPECIFICITY;

EID: 34250820406     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070730c     Document Type: Article

References (44)

1. (a) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. J.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963-972.
2. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308.
3. (c) Callan, J. F.; de Silva, A. P.; Magri, D. C. Tetrahedron 2005, 61, 8551-8588.
4. (a) Kelly, T. R. Acc. Chem. Res. 2001, 34, 514-522.
5. (b) Kay, E. R.; Leigh, D. A; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191.
6. (c) Browne, W. R.; Feringa, B. L. Nat. Nanotechnol. 2006, 1, 25-35.
7. (d) Badjic, J. D.; Balzani, V.; Credi, A.; Silvi, S.; Stoddart, J. F. Science 2004, 303, 1845-1849.
8. (a) Wu, A.; Isaacs, L. J. Am. Chem. Soc. 2003, 125, 4831-4835.
9. (b) Wu, A.; Chakraborty, A.; Fettinger, J. C.; Flowers, R. A., II; Isaacs, L. Angew. Chem., Int. Ed. 2002, 41, 4028-4031.
10. (c) Mukhopadhyay, P.; Wu, A.; Isaacs, L. J. Org. Chem. 2004, 69, 6157-6164.
11. (d) Mukhopadhyay, P.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2006, 128, 14093-14102.
12. (a) Xu, H.; Hong, R.; Tongxiang, U.; Uzun, O.; Rotello, V. J. Am. Chem. Soc. 2006, 128, 3162-3163.
13. (b) Saur, I.; Scopelliti, R.; Severin, K. Chem.-Eur. J. 2006, 12, 1058-1066.
14. (c) Burd, C.; Week, M. Macromolecules 2005, 38, 7225-7230.
15. (d) Hwang, I.-W.; Kamada, T.; Ahn, T. K.; Ko, D. M.; Nakamura, T.; Tsuda, A.; Osuka, A.; Kim, D. J. Am. Chem. .' Soc. 2004, 126, 16187-16198.
16. (e) Telfer, S. G.; Sato, T.; Kuroda, R.; Lefebvre, D. B. Inorg. Chem. 2004, 43, 421-429 .
17. (f) Bilgicer, B.; Xing, X.; Kumar, K. J. Am. Chem. Soc. 2001, 123, 11815-11816.
18. (g) Taylor, P. N.; Anderson, H. L. J. Am. Chem. Soc. 1999, 121, 11538-11545.
19. (h) Rowan, S. J.; Hamilton, D. G.; Brady, P. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1997, 119, 2578-2579.
20. (i) Kramer, R.; Lehn, J.-M.; Marquis-Rigault, A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5394-5398.
21. (j) Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103-112.
22. (k) Kamada, T.; Aratani, N.; Ikeda, T.; Shibata, N.; Higuchi, Y.; Wakamiya, A.; Yamaguchi, H.; Kim, K. S.; Yoon, Z. S.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2006,128, 76707678.
23. (l) He, Y.; Tian, Y.; Chen, Y.; Ribbe, A. E.; Mao, C. Chem. Commun. 2006, 165-167.
24. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875-1917.
25. (a) Lagona, J.; Mukhopadnyay, P.; Chakrabarti, S.; Isaacs, L. Angew. Chem., Int. Ed. 2005, 44, 4844-4870.
26. (b) Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, 621-630.
27. (a) Mock, W. L.; Shih, N.-Y. J. Org. Chem. 1986, 51, 4440-4446.
28. (b) Liu, S.; Ruspic, C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 15959-15967.
29. (c) Jeon, W. S.; Moon, K.; Park, S. H.; Chun, H.; Ko, Y. H.; Lee, J. Y.; Lee, E. S.; Samal, S.; Selvapalam, N.; Rekharsky, M. V.; Sindelar, V.; Sobransingh, D.; Inoue, Y.; Kaifer, A. E.; Kim, K. J. Am. Chem. Soc. 2005, 127, 12984-12989.
30. (a) Mock, W. L.; Pierpont, J. J. Chem. Soc., Chem. Commun. 1990, 1509-1511.
31. (b) Jun, S. I.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Tetrahedron Lett. 2000, 41, 471-475.
32. (c) Lee, J. W.; Kim, K.; Kim, K. Chem. Commun. 2001, 1938-1939.
33. (d) Sindelar, V.; Kaifer, A. E. Chem. Commun. 2006, 2185-2187.
34. (e) Sobransingh, D.; Kaifer, A. E. Org. Lett. 2006, 8, 3247-3250.
35. The pH switching experiments performed with mixtures of CB[6], 1, and 2 showed comparable efficiency (Supporting Information).
36. Fast exchange between the β-CD complexes and significant spectral overlap made independent determination of [β-CD·1] and [β-CD·2] challenging. The equal but opposite preference of β-CD based on mass balance considerations assumes the concentration of free β-CD is small, which seems reasonable given its high affinity toward adamantane derivatives (ref 5).
37. a shifts in CB[n], complexes see: Mohanty, J.; Bhasikuttan, A. C.; Nau, W. M.; Pal, H. J. Phys. Chem. B 2006, 110, 5132-5138.
38. (a) GEPASI can be downloaded free of charge at http://www.gepasi.org.
39. (b) Mendes, P. Comput. Appl. Biosci. 1993, 9, 563-571.
40. (c) Mendes, P. Trends Biochem. Sci. 1997, 22, 361-363.
41. (d) Mendes, P.; Kell, D. B. Bioinformatics 1998, 14, 51-67.
42. + (Supporting Information).
43. -1).
44. -1. decomplexation begins to become an issue.