Anion directed synthesis of a hydrogensulfate selective luminescent rotaxane

Chemical Communications

Volumn , Issue 14, 2005, Pages 1909-1911

  Curiel, David ^a   Beer, Paul D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BISULFATE SODIUM; RHENIUM; ROTAXANE; SULFATE; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; LUMINESCENCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ANALYSIS;

EID: 17544378825     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418878k     Document Type: Article

References (36)

1. (a) D. Philp and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1996, 35, 1154;
2. (b) G. A. Breault, C. A. Hunter and P. C. Mayers, Tetrahedron, 1999, 55, 5265;
3. (c) F. M. Raymo and J. F. Stoddart, Chem. Rev., 1999, 99, 1643;
4. (d) T. J. Hubin and D. H. Busch, Coord Chem. Rev., 2000, 200-202, 5.
5. (a) J.-C. Chambron, C. O. Dietrich-Buchecker, J.-F. Nierengarten and J.-P. Sauvage, J. Chem. Soc., Chem. Commun., 1993, 801;
6. (b) C. Hamann, J.-M. Kern and J.-P. Sauvage, Dalton Trans., 2003, 3779;
7. L. Hogg, D. A. Leigh, P. J. Lusby, A. Morelli, S. Parsons and J. K. Y. Wong, Angew. Chem., Int. Ed., 2004, 43, 1218.
8. (a) P. R. Ashton, M. Grognuz, A. M. Z. Slawin, J. F. Stoddart and D. J. Williams, Tetrahedron Lett., 1991, 32, 6235;
9. (b) P. R. Ashton, E. J. T. Chrystal. P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 709;
10. (c) S. J. Loeb and J. A. Wisner, Angew. Chem., Int. Ed., 1998, 37, 2838.
11. (a) C. A. Hunter, J. Am. Chem. Soc., 1992, 114, 5303;
12. (b) F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott and T. Schmidt, Liebigs Ann., 1995, 739;
13. A. G. Johnston, D. A. Leigh, A. Murphy, J. P. Smart and M. D. Deegan, J. Am. Chem. Soc., 1996, 118, 10662.
14. (a) J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1992, 31, 846;
15. (b) Y. Kawaguchi and A. Harada, J. Am. Chem. Soc., 2000, 122, 3797.
16. P. D. Beer and P. A. Gale, Angew. Chem., Int. Ed., 2001, 40, 486.
17. (a) J. S. Fleming, K. L. V. Mann, C.-A. Carraz, E. Psillakis, J. C. Jeffery, J. A. McCleverty and M. D. Ward, Angew. Chem., Int. Ed., 1998, 37, 1279;
18. (b) R. L. Paul, Z. R. Bell, J. C. Jeffery, J. A. McCleverty and M. D. Ward, Proc. Natl. Acad. Sci. USA, 2002, 99, 4883.
19. (a) B. Hasenknopf, J.-M. Lehn, B. O. Kneisel, G. Baum and D. Fenske, Angew. Chem., Int. Ed., 1998, 37, 1279;
20. B. Hasenknopf, J.-M. Lehn, N. Boumediene, A. Dupont-Gervais, A. Van Dorsselaer, B. Kneisel and D. Fenske, J. Am. Chem. Soc., 1997, 119, 10956.
21. R. Vilar, Angew. Chem., Int. Ed., 2003, 42, 1460.
22. (a) M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White and D. J. Williams, Angew. Chem., Int. Ed. Engl., 1997, 36, 2068;
23. (b) C. Seel and F. Vögtle, Chem. Eur. J., 2000, 6, 21;
24. (c) M. J. Deetz, R. Shukla and B. D. Smith, Tetrahedron, 2002, 58, 799.
25. (a) J. A. Wisner, P. D. Beer and M. G. D. Drew, Angew. Chem., Int. Ed., 2001, 40, 3606;
26. (b) J. A. Wisner, P. D. Beer, N. G. Berry and B. Tomapatanaget, Proc. Natl. Acad. Sci. USA, 2002, 99, 4983;
27. (c) D. Curiel, P. D. Beer, R. L. Paul, A. Cowley, M. R. Sambrook and F. Szemes, Chem. Commun., 2004, 1162.
28. J. A. Wisner, P. D. Beer, M. G. D. Drew and M. R. Sambrook, J. Am. Chem. Soc., 2002, 124, 12469.
29. M. R. Sambrook, P. D. Beer, J. A. Wisner, R. L. Paul and A. R. Cowley, J. Am. Chem. Soc., 2004, 126, 15364.
30. R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413.
31. E. Kelderman, L. Derhaeg, G. R. T. Heesink, W. Verboom, J. F. J. Engbersen, N. F. V. Hulst, A. Persoons and D. N. Reindhout, Angew. Chem., Int. Ed. Engl., 1992, 31, 1075.
32. (a) P. D. Beer, F. Szemes, V. Balzani, C. M. Salá, M. G. W. Drew, S. W. Dent and M. Maestri, J. Am. Chem. Soc., 1997, 119, 11864;
33. (b) L. H. Uppadine, J. E. Redman, S. W. Dent, M. G. B. Drew and P. D. Beer, Inorg. Chem., 2001, 40, 2860.
34. R. A. Binstead, B. Jung and A. D. Zuberbühler, Specfit/32, © 2000, Spectrum Software Associates, Marlborough, MA, USA.
35. J. L. Sessler, E. Katayev, G. Dan Pantos and Y. A. Ustynyuk, Chem. Commun., 2004, 1276.
36. Fluorescence titrations experiments of 11 with TBA dihydrogenphosphate also caused significant enhancement of emission intensity suggesting strong complexation of this tetrahedral anion guest. Specfit analysis of the resulting titration curves however failed to give an association constant value.