Complexation between Pentiptycene Derived Bis(crown ther)s and CBPQT 4〈 Salt: Ion-Controlled Switchable Processes and Changeable Role of the CBPQT4〈in Host-Guest Systems

Journal of Organic Chemistry

Volumn 76, Issue 6, 2011, Pages 1644-1652

  Cao, Jing ^a,b   Guo, Jia Bin ^a,b   Li, Peng Fei ^a,b   Chen, Chuan Feng ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE RING; BINDING AND RELEASE; BIS(CROWN ETHER); HOST-GUEST SYSTEM; PENTIPTYCENE; POTASSIUM IONS; STABLE COMPLEXES; SUPRAMOLECULAR SYSTEMS; SWITCHABLE;

BENZENE; ETHERS; LIGANDS; NAPHTHALENE; ORGANIC COMPOUNDS;

CROWN ETHERS;

BENZENE; CROWN ETHER DERIVATIVE; NAPHTHALENE DERIVATIVE; POTASSIUM ION; SODIUM CHLORIDE; TRIPTYCENE DERIVATIVE;

ARTICLE; BINDING KINETICS; COMPLEX FORMATION; MOLECULAR STABILITY; SOLID STATE; STEREOSPECIFICITY; SUBSTITUTION REACTION; SUPRAMOLECULAR CHEMISTRY;

EID: 79953872090     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102288r     Document Type: Article

References (60)

1. (a)Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vogtle, F., Lehn, J.-M., Eds.; Elsevier: Amsterdam, The Netherlands, 1996.
2. (b) Functional Synthetic Receptors; Schrader, T., Hamilton, A. D., Eds.; Wiley-VCH, Weinheim, Germany, 2005.
3. (c) Macrocyclic Chemistry: Current Trends and Future Perspectives; Gloe, K., Ed.; Springer: Dordrecht, The Netherlands, 2005.
4. (d) Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; John Wiley & Sons: New York, 2009.
5. (a) Some recent reviews: (a) Biros, S. M.; Rebek, J., Jr. Chem. Soc. Rev. 2007, 36, 93-104.
6. (b) Kang, S. O.; Llinares, J. M.; Day, V. W.; Bowman-James, K. Chem. Soc. Rev. 2010, 39, 3980- 4003.
7. (c) Kim, J. S.; Lee, S. Y.; Yoon, J.; Vicens, J. Chem. Commun. 2009, 32, 4791- 4802.
8. (c) Kim, J. S.; Lee, S. Y.; Yoon, J.; Vicens, J. Chem. Commun. 2009, 32, 4791- 4802.
9. (e) Kim, K.; Selvapalam, N.; Ko, Y. H.; Park, K. M.; Kim, D.; Kim, J. Chem. Soc. Rev. 2007, 36, 267- 279.
10. (f) Isaacs, L. Chem. Commun. 2009, 619- 629.
11. (g) Gale, P. A. Chem. Soc. Rev. 2010, 39, 3746- 3771.
12. (h) Albrecht, M.; Stortz, P. Chem. Soc. Rev. 2005, 34, 496- 506.
13. (a) Zhu, X.-Z.; Chen, C.-F. J. Org. Chem. 2005, 70, 917-924.
14. (b) Cao, J.; Lu, H.-Y.; Chen, C.-F. Tetrahedron 2009, 65, 8104- 8112.
15. (c) Yang, J. S.; Yan, J. L. Chem. Commun. 2008, 1501- 1512 and references cited therein.
16. (a)Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 5321-5322.
17. (b) Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864- 11873.
18. (c) Swager, T. M. Acc. Chem. Res. 2008, 41, 1181- 1189 and references cited therein.
19. Yang, J. S.; Yan, J. L.; Lin, C. K.; Chen, C. Y.; Xie, Z. Y.; Chen, C. H. Angew. Chem., Int. Ed. 2009, 48, 9936-9939.
20. (a) Yang, J. S.; Lin, C. S.; Hwang, C. Y. Org. Lett. 2001, 3, 889-892.
21. (b) Zyryanov, G. V.; Palacios, M. A.; Anzenbacher, P., Jr. Org. Lett. 2008, 10, 3681- 3684.
22. (c) Thomas, S. W.; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339- 1386.
23. (a) Yang, J. S.; Lee, C. C.; Yau, S. L.; Chang, C. C.; Lee, C. C.; Leu, J. M. J. Org. Chem. 2000, 65, 871-877.
24. (b) Long, T. M.; Swager, T. M. Adv. Mater. 2001, 13, 601- 604.
25. (c) Long, T. M.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 3826- 3827.
26. (a) Yang, J. S.; Huang, Y. T.; Ho, J. H.; Sun, W. T.; Huang, H. H.; Lin, Y. C.; Huang, S. J.; Huang, S. L.; Lu, H. F.; Chao, I. Org. Lett. 2008, 10, 2279-2282.
27. (b) Sun, W.-T.; Huang, Y.-T.; Huang, G.-J.; Lu, H.-F.; Chao, I.; Huang, S.-L.; Huang, S.-J.; Lin, Y.-C.; Ho, J.-H.; Yang, J.-S. Chem.-Eur. J. 2010, 16, 11594- 11604.
28. (a) Zhu, X.-Z.; Chen, C.-F. J. Am. Chem. Soc. 2005, 127, 13158-13159.
29. (b) Zong, Q.-S.; Chen, C.-F. Org. Lett. 2006, 8, 211- 214.
30. (c) Han, T.; Chen, C.-F. J. Org. Chem. 2007, 72, 7287- 7293.
31. (d) Zhao, J.-M.; Zong, Q.-S.; Han, T.; Xiang, J.-F.; Chen, C.-F. J. Org. Chem. 2008, 73, 6800- 6806.
32. (e) Tian, X.-H.; Chen, C.-F. Chem.-Eur. J. 2010, 16, 8072- 8079.
33. (f) Hu, S.-Z.; Chen, C.-F. Chem. Commun. 2010, 46, 4199- 4201.
34. (g) Tian, X.-H.; Chen, C.-F. Org. Lett. 2010, 12, 524- 527.
35. (h) Jiang, Y.; Chen, C.-F. Chem. Commun. 2010, 46, 5536- 5538.
36. (i) Xue, M.; Su, Y.-S.; Chen, C.-F. Chem.-Eur. J. 2010, 16, 8537- 8544.
37. (a) Cao, J.; Jiang, Y.; Zhao, J.-M.; Chen, C.-F. Chem. Commun. 2009, 1987-1989.
38. (b) Cao, J.; Lu, H.-Y.; You, X.-J.; Zheng, Q.-Y.; Chen, C.-F. Org. Lett. 2009, 11, 4446- 4449.
39. (c) Cao, J.; Lu, H.-Y.; Xiang, J.-F.; Chen, C.-F. Chem. Commun. 2010, 3586- 3588.
40. (d) Cao, J.; Zhu, X.-Z.; Chen, C.-F. J. Org. Chem. 2010, 75, 7420- 7423.
41. Odell, B.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1547-1550.
42. (a) Córdova, E.; Bissell, R. A.; Spencer, N.; Ashton, P. R.; Stoddart, J. F.; Kaifer, A. E. J. Org. Chem. 1993, 58, 6550-6552.
43. (b) Córdova, E.; Bissell, R. A.; Kaifer, A. E. J. Org. Chem. 1995, 60, 1033- 1038.
44. (c) Asakawa, M.; Ashton, P. R.; Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Montalti, M.; Spencer, N.; Stoddart, J. F.; Venturi, M. Chem.-Eur. J. 1997, 3, 1992- 1996.
45. (a) Some recent examples: (a) Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Science 2004, 306, 2055-2056.
46. (b) Liu,Y.; Flood, A. H.; Bonvallet, P. A.; Vignon, S. A.; Northrop, B. H.; Tseng, H. R.; Jeppesen, J. O.; Huang, T. J.; Brough, B.; Baller, M.; Magonov, S.; Solares, S. D.; Goddard, W. A.; Ho, C. M.; Stoddart, J. F. J. Am. Chem. Soc. 2005, 127, 9745- 9759.
47. (c) Deng, W, Q.; Flood, A. H.; Stoddart, J. F.; Goddard, W. A., III J. Am. Chem. Soc. 2005, 127, 15994- 15995.
48. (d) Dichtel, W. R.; Miljanic, O. S.; Zhang, W. Y.; Spruell, J. M.; Patel, K.; Aprahamian, I.; Heath, J. R.; Stoddart, J. F. Acc. Chem. Res. 2008, 41, 1750- 1761.
49. (e) Ikeda, T.; Higuchi, M.; Kurth, D. G. J. Am. Chem. Soc. 2009, 131, 9158- 9159.
50. Jiang, J.; Maclachlan, M. J. Chem. Commun. 2009, 5695-5697.
51. Peng, X.-X.; Lu, H.-Y.; Han, T.; Chen, C.-F. Org. Lett. 2007, 8, 895-898.
52. See the Supporting Information for details.
53. (a) Han, T.; Chen, C.-F. Org. Lett. 2006, 8, 1859-1862.
54. (b) Connors, K. A. Binding Constants; J. Wiley and Sons: New York, 1987.
55. Anelli, P. L.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M. T.; Goodnow, T. T.; Kaifer, A. E.; Philp, D.; Prodi, M. P. L.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Vicent, C.; Williams, D. J. J. Am. Chem. Soc. 1992, 114, 193-218.
56. (a) Balzani, V.; Credi, A.; Mattersteig, G.; Matthews, O. A.; Raymo, F. M.; Stoddart, J. F.; Venturi, M.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 1924-1936.
57. (b) Flood, A. H.; Nygaard, S.; Laursen, B. W.; Jeppesen, J. O.; Stoddart, J. F. Org. Lett. 2006, 8, 2205- 2208.
58. Ikeda, T.; Aprahamian, I.; Stoddart, J. F. Org. Lett. 2007, 9, 1481-1484.
59. (a) Asakawa, M.; Iqbal, S.; Stoddart, J. F.; Tinker, N. D. Angew. Chem., Int. Ed. 1996, 35, 976-978.
60. (b) Han, T.; Zong, Q.-S.; Chen, C.-F. J. Org. Chem. 2007, 72, 3108- 3111.