A simple but effective dual redox and fluorescent ion pair receptor based on a ferrocene-imidazopyrene dyad

Organic Letters

Volumn 13, Issue 8, 2011, Pages 2078-2081

  Alfonso, María ^a   Espinosa, Arturo ^a   Tárraga, Alberto ^a   Molina, Pedro ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955425789     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2004935     Document Type: Article

References (31)

1. Smith, B. D. In Ion Pair Recognition by Ditopic Receptors, Macrocyclic Chemistry: Current Trends and Future; Gloe, K., Antonioli, B., Eds.; Kluwer: London, 2005; pp 137-152.
2. Kirkovits, G. J.; Shiriver, J. A.; Gale, P. A.; Sessler, J. L. J. Inclusion Phenom. Macrocyclic Chem. 2001, 41, 69-75.
3. Kim, S. K.; Sessler, J. L. Chem. Soc. Rev. 2010, 39, 3784-3809.
4. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191-221.
5. Pelizzi, N.; Casnati, A.; Friggeri, A.; Ungaro, R. J. Chem. Soc., Perkin Trans. 2 1998, 1307-1311.
6. White, D. J.; Laing, N.; Millar, H.; Parsons, S.; Coles, S.; Tasker, P. A. Chem. Commun. 1999, 2077-2078.
7. Rudkevich, D. M.; Mercer-Chalmer, J. D.; Verboom, W.; Ungaro, R.; de Jong, F.; Reinhoudt, D. N. J. Am. Chem. Soc. 1995, 117, 6124-6125
8. Reetz, M. T.; Niemeyer, C. M.; Harms, K. Angew. Chem., Int. Ed. 1991, 30, 1472-1474.
9. Custelcean, R.; Delmau, L. H.; Moyer, B. A.; Sessler, J. L.; Cho, W.-S.; Gross, D.; Bates, G. W.; Brooks, S. J.; Light, M. E.; Gale, P. A. Angew. Chem., Int. Ed. 2005, 44, 2537-2542.
10. Mele, A.; Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. J. Am. Chem. Soc. 2005, 127, 14972-14973.
11. Cametti, M.; Nissinen, M.; Dalla Cort, A.; Mandolini, L.; Rissanen, K. J. Am. Chem. Soc. 2007, 129, 3641-3648.
12. Mahoney, J. M.; Beatty, A. M.; Smith, B. D. J. Am. Chem. Soc. 2001, 123, 5847-5848.
13. Miyaji, H.; Collinson, S. R.; Prokeš, I.; Tucker, J. H. R. Chem. Commun. 2003, 64-65.
14. Mahoney, J. M.; Beatty, A. M.; Smith, B. D. Inorg. Chem. 2004, 43, 7617-7621.
15. Mahoney, J. M.; Stucker, K. A.; Jiang, H.; Carmichael, I.; Brinkmann, N. R.; Betty, A. M.; Noll, B. C.; Smith, B. D. J. Am. Chem. Soc. 2005, 127, 2922-2928.
16. Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 3683-3686.
17. Lankshear, M. D.; Cowley, A. R.; Beer, P. D. Chem. Commun. 2006, 612-614.
18. Deetz, M. J.; Shang, M.; Smith, B. D. J. Am. Chem. Soc. 2000, 122, 6201-6207.
19. Shukla, R.; Kida, T.; Smith, B. D. Org. Lett. 2000, 2, 3099-3102.
20. de Silva, A. P.; McClean,G. D.; Pagliari, S. Chem.Commun. 2003, 2010-2011.
21. Hu, J.; Zhang, D.; Harris, F. W. J. Org. Chem. 2005, 70, 707-708.
22. Zapata, F.; Caballero, A.; Espinosa, A.; Tárraga, A.; Molina, P. J. Org. Chem. 2008, 73, 4034-4044.
23. Steck, E. A.; Day, A. R. J. Am. Chem. Soc. 1943, 65, 452-456.
24. OSWV technique has been employed to obtain well-resolved potential information:
25. Serr, B. R.; Andersen, K. A.; Elliot, C. M.; Anderson, O. P. Inorg. Chem. 1988, 27, 4499-4504.
26. Richardson, D. E.; Taube, H. Inorg. Chem. 1981, 20, 1278-1285.
27. Specfit/32 Global Analysis System, 1999-2004; Spectrum Software Associates: Singapore, 1999-2004; http:www.bio-logic.info/spectfitsup/ index.html.
28. From the titration data, the ? values were found to be of the same order as those found in the titration of the free receptor.
29. Gale, P. A.; Hursthouse, M. B.; Light, M. E.; Sessler, J. L. Tetrahedron Lett. 2001, 42, 6759-6762.
30. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University Press: Oxford, 1990.
31. Figure 5 was generated with AMD: Humphrey, W.; Dalke, A.; Schulten, K. J. Molec. Graphics 1996, 14, 33-38 (http://www.ks.uiuc. edu/Research/vmd/).