Duplexiphane: A polyaromatic receptor containing two adjoined Δ-shaped cavities for an efficient hopping of a single silver cation

Organic Letters

Volumn 10, Issue 3, 2008, Pages 389-392

  Emond, Susanna J ^a   Debroy, Paromita ^a   Rathore, Rajendra ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 38949106877     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7026762     Document Type: Article

References (28)

1. (a) Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59.
2. (b) Ikeda, M.; Tanida, T.; Takeuchi, M.; Shinkai, S. Org. Lett. 2000, 2, 1803.
3. (c) Lindeman, S. V.; Rathore, R.; Kochi, J. K. Inorg. Chem. 2000, 39, 5707 and references therein.
4. (a) Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitachek, P.; Lehne, V. J. Org. Chem. 1993, 58, 2781.
5. (b) Gano, J. E.; Subramaniam, G.; Birnbaum, R. J. Org. Chem. 1990, 55, 4760.
6. (c) Yang, R.-H.; Chan, W.-H.; Lee, A. W. M.; Xia, P.-F.; Zhang, H.-K.; Li, K. J. Am. Chem. Soc. 2003, 125, 2884.
7. (d) Rathore, R.; Chebny, V. J.; Abdelwahed, S. H. J. Am. Chem. Soc. 2004, 127, 8012.
8. (a) Munakata, M.; Wu, L. P.; Kuroda-Sowa, T.; Maekawa, M.; Suenaga, Y.; Sugimoto, K. Inorg. Chem. 1997, 36, 4903.
9. (b) Munakata, M.; Wu, L. P.; Ning, G. L.; Kuroda-Sowa, T.; Maekawa, M.; Suenaga, Y.; Macao, Y. J. Am. Chem. Soc. 1999, 121, 4968.
10. (a) Pierre, J. L.; Baret, P.; Chautemps, P.; Armand, M. J. Am. Chem. Soc. 1981, 103, 2986.
11. (b) Kang, H. C.; Hanson, A. W.; Eaton, B.; Boelelheide, V. J. Am. Chem. Soc. 1985, 107, 1979.
12. (c) Pierre, G.; Baret, P.; Chautemps, P.; Pierre, J. L. Electrochim. Acta 1983, 28, 1269.
13. (c) Schmidbaur, H.; Hager, R.; Huber, B.; Muller, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 338.
14. (d) Probst, T.; Steigelmann, O.; Riede, J.; Schmidbaur, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1397.
15. (a) Petty, M. C.; Bryce, M. R. In Introduction to Molecular Electronics; Bloor, D., Ed.; Oxford University Press: New York, 1995.
16. (b) Maiya, B. G.; Ramasarma, T. Curr. Sci. 2001, 80, 1523.
17. Compare: Heirtzler, F. R.; Hopf, H.; Jones, P. G.; Bubenitschek, P. Tetrahedron Lett. 1995, 36, 1239.
18. The term "duplexiphane" was coined based on the suggestion by our colleague James R. Kincaid who pointed out that the structure of 3 conceptually resembles that of a "duplex", a house partitioned to accom-modate two residents.
19. For other examples of metal-ion hopping, see: (a) Ohseto, F.; Sakaki, T.; Araki, K.; Shinkai, S. Tetrahedron Lett. 1993, 34, 2149.
20. (b) Walker, A. V.; Tighe, T. B.; Cabarcos, O. M.; Reinard, M. D.; Haynie, B. C.; Uppili, S.; Winograd, N.; Allara, D. L. J. Am. Chem. Soc. 2004, 126, 3954.
21. (c) Berg, D. J.; Sun, J.; Twamley, B. Chem. Commun. 2006, 4019.
22. Du, C. J. F.; Hart, H.; Ng, K. K. D. J. Org. Chem. 1986, 51, 3162.
23. 4b to be much faster than NMR time scale at 22 °C, i.e. >200 Hz.
24. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy: A Guide for Chemists; Oxford University Press: New York, 1993, pp 205-234.
25. -1.
26. The synthetic details and X-ray crystallographic structural characterization of the model receptor 9 will be published separately.
27. (a) Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723.
28. (b) Weber, M. E.; Gokel, G. W.; Leevy, W. M.; Hughes-Strange, G. B.; Daranciang, D. D.; Ferdani, R.; Gokel, M. R. Org. Biomol. Chem. 2005, 3, 1647.