Facile synthesis of cucurbit[n]uril derivatives via direct functionalization: Expanding utilization of cucurbit[n]uril

Journal of the American Chemical Society

Volumn 125, Issue 34, 2003, Pages 10186-10187

  Jon, Sang Yong ^a   Selvapalam, Narayanan ^a   Oh, Dong Hyun ^a   Kang, Jin Koo ^a   Kim, Soo Young ^a   Jeon, Young Jin ^a   Lee, Jae Wook ^a   Kim, Kimoon ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CUCURBITURIL; DIMETHYL SULFOXIDE; MACROCYCLIC COMPOUND; NANOPARTICLE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; MOLECULAR DYNAMICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS;

EID: 0041429631     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036536c     Document Type: Article

References (43)

1. Mock, W. L. In Comprehensive Supramolecular Chemistry Vögtle, Ed.; Pergamon: Oxford, 1996; Vol. 2, p 477.
2. (a) Whang, D.; Jeon, Y.-M.; Heo, J.; Kim, K. J. Am. Chem. Soc. 1996, 118, 11333.
3. (b) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451.
4. (c) Whang, D.; Park, K.-M.; Heo, J.; Ashton, P.; Kim, K. J. Am. Chem. Soc. 1998. 120, 4899.
5. (d) Roh, S.-G.; Park, K.-M.; Sakamoto, S.; Tamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 1999, 38, 638.
6. (e) Lee, E.; Heo J.; Kim, K. Angew. Chem., Int. Ed. 2000, 39, 2699.
7. (f) Lee, E.; Kim, J.; Heo, J.; Whang, D.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 399.
8. (g) Lee, J. W.; Ko, Y. H.; Park, S.-H.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 746.
9. (h) Park, K.-M.; Whang, D.; Lee, E.; Heo, J.; Kim, K. Chem.-Eur. J. 2002, 8, 498.
10. (i) Park, K.-M.; Kim, S.-Y.; Heo, J.; Whang, D.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2002, 124, 2140.
11. (j) Kim, K. Chem. Soc. Rev. 2002, 31, 96.
12. (k) Lee, J. W.; Kim, K. Top. Curr. Chem. 2003, 228, 111.
13. (l) Lee, J. W.; Choi, S. W.; Ko, Y. H.; Kim, S.-Y.; Kim, K. Bull. Korean Chem. Soc. 2002, 23, 1347.
14. (a) Hoecker, H.; Buschmann, H.-J. Macromol. Rapid Commun. 1998, 19, 59.
15. (b) Tuncel, D.; Steinke, J. H. G. Chem. Commun. 1999, 1509.
16. (c) Meschke, C.; Buschmann, H.-J.; Schollmeyer, E. Polymer 1999, 40, 945.
17. (d) Sokolov, M. N.; Virovets, A. V.; Dybtsev, D. N.; Gerasko, O. A.; Fedin, V. P.; Hernandez-Molina, R.; Clegg, W.; Sykes, A. G. Angew. Chem., Int. Ed. 2000, 39, 1659.
18. (e) Tuncel D.; Steinke, J. H. G. Chem. Commun. 2001, 253.
19. Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. J. Am. Chem. Soc. 2000, 122, 540.
20. (a) Kim, H.-J.; Heo, J.; Jeon, W. S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 1526.
21. (b) Kim, S.-Y.; Jung, I.-S.; Lee, E.; Kim, J.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 2119.
22. (c) Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H.-J.; Kim, K. Chem. Commun. 2001, 1938.
23. (d) Kim, H.-J.; Jeon, W. S.; Ko, Y. H.; Kim, K. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5007.
24. (e) Jeon, Y. J.; Bharadwaj, P. K.; Choi, S. W.; Lee, J. W.; Kim, K. Angew. Chem., Int. Ed. 2002, 41, 4474.
25. (a) Day, A. I.; Arnold, A. P.; Blanch, R. J.; Snushall, B. J. Org. Chem. 2001, 66, 8094.
26. (b) Day, A. I.; Blanch, R. J.; Arnold, A. P.; Lorenzo, S.; Lewis, G. R.; Dance, I. Angew. Chem., Int. Ed. 2002, 41, 275.
27. (c) Marqiez, C.; Nau, W. M. Angew. Chem., Int. Ed. 2001, 40, 4387.
28. (d) Ong, W.; Kaifer, A. E. Angew. Chem., Int. Ed. 2003, 42, 2164.
29. (e) Ong, W.; Gomez-Kaifer, M.; Kaifer, A. E. Org. Lett. 2002, 4, 1791.
30. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Acc. Chem. Res. 2003, 36, ASAP on 05/23/03; DOI: 10.1021/ar020254k.
31. Karcher, S.; Kornmüller, A.; Jekel, M. Water Res. 2001, 35, 3309.
32. (a) Flinn, A.; Hough, G. C.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1992, 31, 1475.
33. (b) Zhao, J.; Kim, H.-J.; Oh, J.; Kim, S.-Y.; Lee, J. W.; Sakamoto, S.; Yamaguchi, K.; Kim, K. Angew. Chem., Int. Ed. 2001, 40, 4233.
34. (a) Isobe, H.; Sato, S.; Nakamura, E. Org. Lett. 2002, 4, 1287.
35. (b) Day, A. I.; Arnold, A. P.; Blanch, R. J. Molecules 2003, 8, 74.
36. +]; satisfactory elemental analysis was obtained for compound 1.
37. See Supporting Information.
38. 16CB[8] have been characterized by NMR and mass spectrometry (see Supporting Information). The improved synthesis and further characterization of the compounds are in progress.
39. (a) Price, J. G.; Clifton, A. A. Polymer 1996, 37, 3971.
40. (b) Lin, H. R. Eur. Polym. J. 2001, 37, 1507.
41. Jiahong, N.; Suddham, S.; Lai-Xi, W. Carbohydr. Res. 2002, 337, 217.
42. Jeon, N. L.; Nuzzo, R. G.; Xia, Y.; Mrksich, M.; Whitesides, G. M. Langmuir 1995, 11, 3024.
43. Fu, K.; Klibanov, A. M.; Langer, R. Nat. Biotechnol. 2000, 18, 24.