Electron transfer prompted ejection of a tightly bound K+ from the ethereal cavity of a hexaarylbenzene-based receptor

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1291-1294

  Shukla, Ruchi ^a   Lindeman, Sergey V ^a   Rathore, Rajendra ^a  

^a Marquette University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34147152204     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070122x     Document Type: Article

References (23)

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2. (b) Rathore, R.; Burns, C. L. J. Org. Chem. 2003, 68, 4071 and references therein.
3. (a) Introduction to Molecular Electronics; Petty, M. C., Bryce, M. R., Bloor, D., Eds.; Oxford University Press: New York, 1995.
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5. (a) Rathore, R.; Burns, C. L; Abdelwahed, S. H. Org. Lett. 2004, 6, 1689.
6. (b) Chebny, V. J.; Shukla, R.; Rathore, R. J. Phys. Chem. B 2006, 110, 13003.
7. Lambert, C. Angew. Chem., Int. Ed. 2005, 44, 7337 and references therein.
8. (a) Rathore, R.; Burns, C. L.; Deselnicu, M. I. Org. Lett. 2001, 3, 2887.
9. (b) Chebny, V. J.; Dhar, D.; Lindeman, S. V.; Rathore, R. Org. Lett. 2006, 8, 5401.
10. Compare: Pepermans, H.; Willem, R.; Gielen, M.; Hoogzand, C. J. Org. Chem. 1986, 51, 301.
11. Shukla, R.; Lindeman, S. V.; Rathore, R. J. Am. Chem. Soc. 2006, 128, 5328.
12. Shukla, R.; Lindeman, S. V.; Rathore, R. J. Org. Chem. 2006, 71, 6124.
13. (a) Osteryoung, J. G.; Osteryoung, R. A. Anal. Chem. 1985, 57, 101A.
14. 5
15. Compare: (a) Dubois, D.; Kadish, K. M.; Flanagan, S.; Wilson, L. J. J. Am. Chem. Soc. 1991, 113, 7773.
16. (b) Blackstock, S. C; Selby, T. D. J. Am. Chem. Soc. 1998, 120, 12155.
17. (a) It should be noted that the observed lowering of the first oxidation potential in 9u/9s does not arise due to the mediation of the central benzene ring because of the fact that 1,4-bis(2,5-dimethoxytolyl)durene ejects both of its electrons at a potential of 1.16 V vs SCE. See: Sun, D.; Lindeman, S. V.; Rathore, R.; Kochi, J. K. J. Chem. Soc., Perkin Trans. 2 2001, 1585.
18. Also see: (b) Rathore, R.; Abdelwahed, S. H.; Guezi, I. A. J. Am. Chem. Soc. 2003, 125, 8712.
19. (c) Rathore, R.; Chebny, V. J.; Kopatz, E. J.; Guezi, I. A. Angew. Chem., Int. Ed. 2005, 44, 2771.
20. The nature of electronic coupling, i.e., toroidal delocalization vs Coulombic repulsion among the circularly arrayed aryl groups in oxidized 9s/9u, is presently under investigation.
21. Competition experiments indicated that 9s and [18]crown-6 have a comparable affinity for the potassium cation.
22. Note that a positive charge in a para-hydroquinone ether stabilizes by a quinoidal distortion where a cationic charge is found largely on the ethereal oxygens. See ref 11a.
23. Ross, S. E.; Shi, Y.; Seliskar, C. J.; Heineman, W. R. Electrochim. Acta 2003, 48, 3313 and references therein.