Formation of 1:2 host-guest complexes based on triptycene-derived macrotricycle and paraquat derivatives: Anion-π Interactions between PF 6 - and bipyridinium rings in the solid state

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5688-5691

  Guo, Jia Bin ^a,b   Han, Ying ^a,b   Cao, Jing ^a   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

ANTHRACENE DERIVATIVE; CROWN ETHER; DIBENZO 30 CROWN 10; DIBENZO-30-CROWN-10; DRUG DERIVATIVE; PARAQUAT; POTASSIUM; TRIPTYCENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

ANTHRACENES; CROWN ETHERS; CRYSTALLOGRAPHY, X-RAY; MOLECULAR STRUCTURE; PARAQUAT; POTASSIUM;

EID: 80054710131     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2024168     Document Type: Article

References (43)

1. Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vogtle, F., Lehn, J.-M., Eds.; Elsevier: The Netherlands, 1996.
2. Steed, J. W.; Atwood, J. L. Supramolecular Chemistry; John Wiley & Sons: 2009.
3. Niu, Z.; Gibson, H. W. Chem. Rev. 2009, 109, 6024-6046
4. Fang, L.; Olson, M. A.; Benitez, D.; Tkatchouk, E.; Goddard, W. A.; Stoddart, J. F. Chem. Soc. Rev. 2010, 39, 17-29
5. Ko, Y. H.; Kim, E.; Hwang, I.; Kim, K. Chem. Commun. 2007, 1305-1315 and references therein
6. Yoshizawa, M.; Tamura, M.; Fujita, M. Science 2006, 312, 251-254
7. Liu, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 127, 16798-16799
8. Sindelar, V.; Cejas, M. A.; Raymo, F. M.; Chen, W.; Parker, S. E.; Kaifer, A. E. Chem.-Eur. J. 2005, 11, 7054-7059
9. Ling, Y.; Wang, W.; Kaifer, A. E. Chem. Commun. 2007, 610-612
10. Han, T.; Chen, C.-F. Org. Lett. 2007, 9, 4207-4210
11. Liu, S.; Shukla, A. D.; Gadde, S.; Wagner, B. D.; Kaifer, A. E.; Isaacs, L. Angew. Chem., Int. Ed. 2008, 47, 2657-2660
12. Ding, Z.-J.; Zhang, H.-Y.; Wang, L.-H.; Ding, F.; Liu, Y. Org. Lett. 2011, 13, 856-859
13. 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, 540-541
14. Yoshizawa, M.; Nakagawa, J.; Kurnazawa, K.; Nagao, M.; Kawano, M.; Ozeki, T.; Fujita, M. Angew. Chem., Int. Ed. 2005, 44, 1810-1813
15. Ono, K.; Yoshizawa, M.; Kato, T.; Watanabe, K.; Fujita, M. Angew. Chem., Int. Ed. 2007, 46, 1803-1806
16. Blanco, V.; Chas, M.; Abella, D.; Pía, E.; Platas-Iglesias, C.; Peinador, C.; Quintela, J. M. Org. Lett. 2008, 10, 409-412
17. Ogoshi, T.; Tanaka, S.; Yamagishi, T.; Nakamoto, Y. Chem. Lett. 2011, 40, 96-98
18. Huang, F.; Zakharov, L. N.; Rheingold, A. L.; Ashraf-Khorassani, M.; Gibson, H. W. J. Org. Chem. 2005, 70, 809-813
19. Huang, F.; Gibson, H. W. Chem. Commun. 2005, 1696-1698
20. Zhang, M.; Zhu, K.; Huang, F. Chem. Commun. 2010, 46, 8131-8141
21. Mascal, M.; Armstrong, A.; Bartberger, M. D. J. Am. Chem. Soc. 2002, 124, 6274-6276
22. Quinonero, D.; Garau, C.; Rotger, C.; Frontera, A.; Ballester, P.; Costa, A.; Deya, P. M. Angew. Chem., Int. Ed. 2002, 41, 3389-3392
23. Alkorta, I.; Rozas, I.; Elguero, J. J. Am. Chem. Soc. 2002, 124, 8593-8598
24. Schottel, B. L.; Chifotides, H. T.; Dunbar, K. R. Chem. Soc. Rev. 2008, 37, 68-83 and references therein
25. Gamez, P.; Mooibroek, T. J.; Teat, S. J.; Reedijk, J. Acc. Chem. Res. 2007, 40, 435-444
26. Götz, R. J.; Robertazzi, A.; Mutikainen, I.; Turpeinen, U.; Gamez, P.; Reedijk, J. Chem. Commun. 2008, 3384-3386
27. Wang, D.-X.; Zheng, Q.-Y.; Wang, Q.-Q.; Wang, M.-X. Angew. Chem., Int. Ed. 2008, 47, 7485-7488
28. Hung, C.-Y.; Singh, A. S.; Chen, C.-W.; Wen, Y.-S.; Sun, S.-S. Chem. Commun. 2009, 1511-1513
29. Wang, D.-X.; Wang, Q.-Q.; Han, Y.; Wang, Y.; Huang, Z.-T.; Wang, M.-X. Chem.-Eur. J. 2010, 16, 13053-13057
30. Müller, M.; Albrecht, M.; Gossen, V.; Peters, T.; Hoffmann, A.; Raabe, G.; Valkonen, A.; Rissanen, K. Chem.-Eur. J. 2010, 16, 12446-12453
31. Albrecht, M.; Müller, M.; Mergel, O.; Rissanen, K.; Valkonen, A. Chem.-Eur. J. 2010, 16, 5062-5069
32. Guha, S.; Saha, S. J. Am. Chem. Soc. 2010, 132, 17674-17677
33. Mooibroek, T. J.; Black, C. A.; Gamez, P.; Reedijk, J. Cryst. Growth Des. 2008, 8, 1082-1093
34. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516
35. Estarellas, C.; Frontera, A.; Quiñonero, D.; Deyà, P. M. Angew. Chem., Int. Ed. 2011, 50, 415-418
36. de Hoog, P.; Gamez, P.; Mutikainen, H.; Turpeinen, U.; Reedijk, J. Angew. Chem., Int. Ed. 2004, 43, 5815-5817
37. A recent review for synthesis and applications of novel triptycene-derived hosts: Chen, C.-F. Chem. Commun. 2011, 47, 1674-1688
38. Zhao, J.-M.; Zong, Q.-S.; Chen, C.-F. J. Org. Chem. 2010, 75, 5092-5098
39. Zong, Q.-S.; Chen, C.-F. Org. Lett. 2006, 8, 211-214
40. Han, T.; Zong, Q.-S.; Chen, C.-F. J. Org. Chem. 2007, 72, 3108-3111
41. Connors, K. A. Binding Constants; J. Wiley and Sons: New York, 1987.
42. Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 7017-7036
43. Inoue, Y.; Liu, Y.; Tong, L.-H; Ouchi, M.; Hakushi, T. J. Chem. Soc., Perkin Trans. 2 1993, 1947-1950