A novel phosphate chemosensor utilizing anion-induced fluorescence change

Organic Letters

Volumn 4, Issue 4, 2002, Pages 561-564

  Liao, Jen Hai ^a   Chen, Chao Tsen ^a   Fang, Jim Min ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORESCENT DYE; N,N' BIS(3,5 DI ((1 PYRENYLMETHYL)CARBAMOYL)BENZYL)PYRIDINE 2,6 DICARBAMIDE; N,N'-BIS(3,5-DI-((1-PYRENYLMETHYL)CARBAMOYL)BENZYL)PYRIDINE-2,6-DICARBAMIDE; PHOSPHATE; PYRENE DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROFLUOROMETRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; FLUORESCENCE; FLUORESCENT DYES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PHOSPHATES; PYRENES; PYRIDINES; SPECTROMETRY, FLUORESCENCE;

EID: 0037149071     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0171564     Document Type: Article

References (45)

1. (a) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80.
2. (b) Watanabe, S.; Onogawa, O.; Komatsu, Y.; Yoshida, K. J. Am. Chem. Soc. 1998, 120, 229-230.
3. (c) Beer, P. D.; Cadman, J.; Lloris, J. M.; Martínez-Máñez, R.; Padilla, M. E.; Pardo, T.; Smith, D. K.; Soto, J. J. Chem. Soc., Dalton Trans. 1999, 127-133.
4. (d) Beer, P. D.; Cadman, J. New J. Chem. 1999, 23, 347-349.
5. (e) Anzenbacher, P., Jr.; Jursíková, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 9350-9351.
6. (f) Miyaji, H.; Sessler, J. L. Angew. Chem., Int. Ed. 2001, 40, 154-157.
7. (g) Sancenón, F.; Descalzo, A. B.; Martínez-Máñez, R.; Miranda, M. A.; Soto, J. Angew. Chem., Int. Ed. 2001, 40, 2640-2643.
8. Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
9. Marecek, J. F.; Fischer, P. A.; Burrows, C. J. Tetrahedron Lett. 1988, 29, 6231-6234.
10. (a) Nishizawa, S.; Bühlmann, P.; Iwao, M.; Umezawa, Y. Tetrahedron Lett. 1995, 36, 6483-6486.
11. (b) Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647-1654.
12. (c) Sasaki, S.; Mizuno, M.; Naemura K.; Tobe, Y. J. Org. Chem. 2000, 65, 275-283.
13. (d) Xie, H.; Yi, S.; Yang, X.; Wu, S. New J. Chem. 1999, 23, 1105-1110.
14. (e) Snellink-Ruël, B. H. M.; Antonisse, M. M. G.; Engbersen, J. F. J.; Timmerman, P.; Reinhoudt, D. N. Eur. J. Org. Chem. 2000, 165-170.
15. (a) Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255-3258.
16. (b) Beer, P. D.; Graydon, A. R.; Sutton, L. R. Polyhedron 1996, 15, 2457-2461.
17. (c) Szemes, F.; Hesek, D.; Chen, Z.; Dent, S. W.; Drew, M. G. B.; Goulden, A. J.; Graydon, A. R.; Grieve, A.; Mortimer, R. J.; Wear, T.; Weightman, J. S. Beer, P. D. Inorg. Chem. 1996, 35, 5868-5879.
18. (d) Beer, P. D.; Szemes, F.; Balzani, V.; Salà, C. M.; Drew, M. G. B.; Dent, S. W.; Maestri, M. J. Am. Chem. Soc. 1997, 119, 11864-11875.
19. (e) Beer, P. D.; Timoshenko, V.; Maestri, M.; Passaniti, P.; Balzani, V. Chem. Commun. 1999, 1755-1756.
20. (f) Cooper, J. B.; Drew, M. G. B.; Beer, P. D. J. Chem. Soc., Dalton Trans. 2000, 2721-2728.
21. (g) Hossain, Md. A.; Llinares, J. M.; Powell, D.; Bowman-James, K. Inorg. Chem. 2001, 40, 2936-2937.
22. (a) Galán, A.; de Mendoza, J.; Toiron, C.; Bruix, M.; Deslongchamps, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 9424-9425.
23. (b) Ariga, K.; Anslyn, E. V. J. Org. Chem. 1992, 57, 417-419.
24. (c) Müller, G.; Dürner, G.; Bats, J. W.; Göbel, M. W. Liebigs Ann. Chem. 1994, 1075-1092.
25. (a) Rudkevich, D. M.; Verboom, W.; Brzozka, Z.; Palys, M. J.; Stauthamer, W. P. R. V.; van Hummel, G. J.; Franken, S. M.; Harkema, S.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Am. Chem. Soc. 1994, 116, 4341-4351.
26. (b) Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 443-448.
27. (c) Chrisstoffels, L. A. J.; de Jong, F.; Reinhoudt, D. N. Chem. Eur. J. 2000, 6, 1376-1385.
28. Pyrene has been used as fluorosence probes. For sensing acetate ion according to the mechanism of photoinduced electron transfer, see: (a) Nishizawa, S.; Kaneda, H.; Uchida, T.; Terame, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325-2327. For sensing pyrophosphate-induced self-assembly of (guanidinium)methylpyrene, see:
29. 2+ ions, see:
30. (c) Yang, J.-S.; Lin, C.-S.; Hwang, C.-Y. Org. Lett. 2001, 3, 889-892.
31. Yu, Q.; Baroni, T. E.; Liable-Sands, L.; Rheingold, A. L.; Borovik, A. S. Tetrahedron Lett. 1998, 39, 6831-6834.
32. Bisson, A. P.; Lynch, V. M.; Monahan, M.-K. C.; Anslyn, E. V. Angew. Chem., Int. Ed. Engl. 1997, 36, 2340-2342.
33. Kavallieratos, K.; Bertao, C. M.; Crabtree, R. H. J. Org. Chem. 1999, 64, 1675-1683.
34. Dimick S. M.; Powell, S. C; McMahon, S. A.; Moothoo, D. N.; Naismith, J. H.; Toone, E. J. J. Am. Chem. Soc. 1999, 121, 10286-10296.
35. Connors, K. A. Binding Constants; Wiley: New York, 1987.
36. For application of anion recognition in sensors, see: (a) Snowden, T. S.; Anslyn, E. V. Curr. Opin. Chem. Biol. 1999, 3, 740-746.
37. (b) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516. For use of pyrene as the fluorophore in cation sensing, see:
38. (c) Jin, T.; Ichikawa, K.; Koyama, T. Chem. Commun. 1992, 499-501.
39. (d) Takeshita, M.; Shinkai, S. Chem. Lett. 1994, 125-128.
40. (e) Diamond, D.; McKervey, M. A. Chem. Soc. Rev. 1996, 15-24.
41. (f) Jin, T. Chem. Commun. 1999, 2491-2492. For use of pyrene as the fluorophore in barbital sensing, see:
42. (g) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinkai, S. Chem. Commun. 1992, 1341-134.
43. (h) Aoki, I.; Kawahara, Y.; Sakaki, T.; Harada, T.; Shinkai, S. Bull. Chem. Soc. Jpn. 1993, 66, 927-933.
44. A molecule containing two 2,6-diaminopyridine units linked through an isophthalate spacer forms six hydrogen bonds with barbiturte substrates as shown by the NMR and X-ray analyses. See: Chang, S. K.; Van Engen, D.; Fan, E.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 7640.
45. For a general review of guest molecule induced fluorescence change, see: 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, 1515-1566.