Design and synthesis of a neutral fluorescent macrocyclic receptor for the recognition of urea in chloroform

Organic Letters

Volumn 7, Issue 7, 2005, Pages 1283-1285

  Goswami, Shyamaprosad ^a   Mukherjee, Reshmi ^a,b   Ray, Jayanta ^a  

^a INDIAN INSTITUTE OF ENGINEERING SCIENCE AND TECHNOLOGY   (India)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1,10 PHENANTHROLINE; CHLOROFORM; THIOUREA; UREA;

ARTICLE; BIOSENSOR; COMPLEX FORMATION; FLUORESCENCE; HYDROGEN BOND; REACTION ANALYSIS; SYNTHESIS;

BINDING SITES; CHLOROFORM; FLUORESCENT DYES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SPECTROMETRY, FLUORESCENCE; UREA;

EID: 17444383861     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050034h     Document Type: Article

References (33)

1. (a) De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
2. (b) Fabbrizzi, L. Acc. Chem. Res. 1999, 32, 846.
3. For recent works, see: (c) Mello, J. V.; Finney, N. Angew. Chem., Int. Ed. 2001, 40, 1536. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777. (e) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (f) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. L.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963. (g) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (h) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinki, S. J. Chem. Soc., Chem. Commun. 1992, 1341. (i) Lakowicz, J. R.; Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 257-301.
4. For recent works, see: (c) Mello, J. V.; Finney, N. Angew. Chem., Int. Ed. 2001, 40, 1536. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777. (e) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (f) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. L.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963. (g) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (h) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinki, S. J. Chem. Soc., Chem. Commun. 1992, 1341. (i) Lakowicz, J. R.; Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 257-301.
5. For recent works, see: (c) Mello, J. V.; Finney, N. Angew. Chem., Int. Ed. 2001, 40, 1536. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777. (e) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (f) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. L.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963. (g) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (h) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinki, S. J. Chem. Soc., Chem. Commun. 1992, 1341. (i) Lakowicz, J. R.; Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 257-301.
6. For recent works, see: (c) Mello, J. V.; Finney, N. Angew. Chem., Int. Ed. 2001, 40, 1536. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777. (e) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (f) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. L.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963. (g) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (h) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinki, S. J. Chem. Soc., Chem. Commun. 1992, 1341. (i) Lakowicz, J. R.; Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 257-301.
7. For recent works, see: (c) Mello, J. V.; Finney, N. Angew. Chem., Int. Ed. 2001, 40, 1536. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777. (e) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (f) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. L.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963. (g) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (h) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinki, S. J. Chem. Soc., Chem. Commun. 1992, 1341. (i) Lakowicz, J. R.; Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 257-301.
8. For recent works, see: (c) Mello, J. V.; Finney, N. Angew. Chem., Int. Ed. 2001, 40, 1536. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777. (e) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (f) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. L.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963. (g) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (h) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinki, S. J. Chem. Soc., Chem. Commun. 1992, 1341. (i) Lakowicz, J. R.; Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 257-301.
9. For recent works, see: (c) Mello, J. V.; Finney, N. Angew. Chem., Int. Ed. 2001, 40, 1536. (d) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int. Ed. 2000, 39, 1777. (e) Pugh, V. J.; Hu, Q.-S.; Pu, L. Angew. Chem., Int. Ed. 2000, 39, 3638. (f) Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. L.; Anslyn, E. V. Acc. Chem. Res. 2001, 34, 963. (g) Hartley, J. H.; James, T. D.; Ward, C. J. J. Chem. Soc., Perkin Trans. 1 2000, 3155. (h) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinki, S. J. Chem. Soc., Chem. Commun. 1992, 1341. (i) Lakowicz, J. R.; Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; pp 257-301.
10. Cattarall, R. W. Chemical Sensors; Oxford University Press: New York, 1997; pp 23, 50-53.
11. (a) Hegde, V.; Hung, C.-Y.; Madhukar, P.; Cunningham, R.; Höpfner, T.; Thummel, R. P. J. Am. Chem. Soc. 1993, 115, 872.
12. (b) Hegde, V.; Madhukar, P.; Madura, J. D.; Thummel, R. P. J. Am. Chem. Soc. 1990, 112, 4549.
13. (c) Crego, M.; Marugán, J. J.; Raposo, C.; Sanz, M. J.; Alcázar, V.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1991, 32, 4185.
14. (d) Bell, T. W.; Beckles, D. L.; CraggLiu, P. J.; Maioriello, J.; Papoulis, A. T.; Santora, V. J. In Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; American Chemical Society Books: Washington, DC, 1993; pp 85-103.
15. (e) Bell, T. W.; Liu, J. J. Am. Chem. Soc. 1988, 110, 3673.
16. (f) Bell, T. W.; Hou, Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 1536.
17. (g) Goswami, S. P.; Mukherjee, R. Tetrahedron Lett. 1997, 38, 1619.
18. (h) van Veggel, F. C. J. M.; Reinhoudt, D. N. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Dürr, H., Eds.; VCH: New York, 1991; pp 83-108.
19. (i) van Doorn, A. R.; Schaafstra, R.; Bos, M.; Harkema, S.; van Eerden, J.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1991, 56, 6083.
20. (j) van Staveren, C. J.; Aarts, V. M. L. J.; Grootenhuis, P. D. J.; Droppers, W. J. H.; Van Eerden, J.; Harkema, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 1988, 110, 8134.
21. (k) van Staveren, C. J.; van Eerden, J.; van Veggel, F. C. J. M.; Harkema, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 1988, 110, 4994.
22. Jorgensen, W. L.; Pranata, J. J. Am. Chem. Soc. 1990, 112, 2008.
23. Kelly, T. R.; Bridger, G. J.; Zhao, C. J. Am. Chem. Soc. 1990, 112, 8024.
24. Chandler, C. J.; Deady, L. W.; Reiss, J. A. J. Heterocycl. Chem. 1981, 18, 599.
25. Hansen, D. W., Jr.; Adelstein, G. W. (Searle, G. D., and Co.). Chem. Abstr. 1991, 115, 136387g.
26. (a) Bordell, F. G.; Algrim, D. G.; Harrelson, J. A., Jr., J. Am. Chem. Soc. 1990, 112, 2008.
27. (b) Fan, E.; van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369.
28. (a) Alpha, B.; Lehn, J.-M.; Mathis, G. Angew. Chem., Int. Ed. Engl. 1987, 26, 266.
29. (b) Kalyansundaram, K. Photochemistry of Polypyridines and Porphyrin Complexes; Academic Press: London, 1992; p 92.
30. (a) Colquhoun, H. M.; Goodings, E. P.; Maud, J. M.; Stoddart, J. F.; Wolstenholme, J. B.; Williams, D. J. J. Chem. Soc., Perkin Trans. 2 1985, 607.
31. (b) Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; John Wiley and Sons: New York, 1987; p 340.
32. (c) Roy, J.; Bhattacharya, S.; Ghosh, S.; Mazumder, D.; Bhattacharyya, S. P. Chem. Phys. 1997, 222, 161.
33. (d) Ghosh, P.; Bharadwaj, P. K.; Roy, J.; Ghosh, S. J. Am. Chem. Soc. 1997, 119, 11903.