Direct visual indication of pH windows: 'off-on-off' fluorescent PET (photoinduced electron transfer) sensors/switches

Chemical Communications

Volumn , Issue 21, 1996, Pages 2399-2400

  De Silva, A Prasanna ^a   Gunaratne, H Q Nimal ^a   McCoy, Colin P ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542398697     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002399     Document Type: Article

References (37)

1. L. Stryer, Biochemistry, 3rd edn., Freeman, New York, 1988; M. Crichton, The Andromeda Strain, Knopf, Random House, New York, 1969.
2. L. Stryer, Biochemistry, 3rd edn., Freeman, New York, 1988; M. Crichton, The Andromeda Strain, Knopf, Random House, New York, 1969.
3. (a) R. Y. Tsien, Chem. Eng. News, 1994, July 18, 34;
4. (b) R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire and K. R. A. S. Sandanayake, Chem. Soc. Rev., 1992, 21, 187;
5. (c) Fluorescent Chemosensors for Ion and Molecule Recognition, ed. A. W. Czarnik, ACS Symp. Ser., 1993, 538;
6. (d) B. Valeur, in Probe Design and Chemical Sensing, Top. Fluoresc. Spectrosc., 1994, 4, 21;
7. (e) B. Valeur and E. Bardez, Chem. Br., 1995, 31, 216.
8. (a) Indicators, ed. E. Bishop, Pergamon, Oxford. 1972, discusses the classical 'indicator range' which is quite different from the pH window under discussion;
9. (b) Biochemical Fluorescence: Concepts, vol. 2, ed. R. F. Chen and H. Edelhoch, Marcel Dekker, New York, 1976, discusses several heterocyclic biomolecules which show maxima in their fluorescence-pH profiles. Some of these involve protonation of excited-state fluorophores which does not apply to 1-3.
10. (a) A. P. de Silva, H. Q. N. Gunaratne and C. P. McCoy, Nature, 1993, 364, 42;
11. (b) A. P. de Silva, H. Q. N. Gunaratne and G. E. M. Maguire, J. Chem. Soc., Chem. Commun., 1994, 1231;
12. (c) S. Iwata and K. Tanaka, J. Chem. Soc. Chem. Commun., 1995, 1491;
13. (d) P. Ghosh, P. K. Bharadwaj, S. Mandal and S. Ghosh, J. Am. Chem. Soc., 1996, 118, 1553.
14. M. R. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867; J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. de Cola and L. Flamigni, Chem. Rev., 1994, 94, 993; R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759; G. F. Mes, H. J. van Ramesdonk and J. W. Verhoeven, J. Am. Chem. Soc., 1984, 106, 1335; L. Fabbrizzi, M. Licchelli, P. Pallavicini and A. Taglietti, Inorg. Chem., 1996, 35, 1733.
15. M. R. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867; J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. de Cola and L. Flamigni, Chem. Rev., 1994, 94, 993; R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759; G. F. Mes, H. J. van Ramesdonk and J. W. Verhoeven, J. Am. Chem. Soc., 1984, 106, 1335; L. Fabbrizzi, M. Licchelli, P. Pallavicini and A. Taglietti, Inorg. Chem., 1996, 35, 1733.
16. M. R. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867; J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. de Cola and L. Flamigni, Chem. Rev., 1994, 94, 993; R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759; G. F. Mes, H. J. van Ramesdonk and J. W. Verhoeven, J. Am. Chem. Soc., 1984, 106, 1335; L. Fabbrizzi, M. Licchelli, P. Pallavicini and A. Taglietti, Inorg. Chem., 1996, 35, 1733.
17. M. R. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867; J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. de Cola and L. Flamigni, Chem. Rev., 1994, 94, 993; R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759; G. F. Mes, H. J. van Ramesdonk and J. W. Verhoeven, J. Am. Chem. Soc., 1984, 106, 1335; L. Fabbrizzi, M. Licchelli, P. Pallavicini and A. Taglietti, Inorg. Chem., 1996, 35, 1733.
18. M. R. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867; J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. de Cola and L. Flamigni, Chem. Rev., 1994, 94, 993; R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759; G. F. Mes, H. J. van Ramesdonk and J. W. Verhoeven, J. Am. Chem. Soc., 1984, 106, 1335; L. Fabbrizzi, M. Licchelli, P. Pallavicini and A. Taglietti, Inorg. Chem., 1996, 35, 1733.
19. M. R. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867; J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. de Cola and L. Flamigni, Chem. Rev., 1994, 94, 993; R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759; G. F. Mes, H. J. van Ramesdonk and J. W. Verhoeven, J. Am. Chem. Soc., 1984, 106, 1335; L. Fabbrizzi, M. Licchelli, P. Pallavicini and A. Taglietti, Inorg. Chem., 1996, 35, 1733.
20. M. R. Wasielewski, Chem. Rev., 1992, 92, 435; D. Gust, T. A. Moore and A. L. Moore, Acc. Chem. Res., 1993, 26, 198; K. Maruyama, A. Osuka and N. Mataga, Pure Appl. Chem., 1994, 66, 867; J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. de Cola and L. Flamigni, Chem. Rev., 1994, 94, 993; R. W. Wagner and J. S. Lindsey, J. Am. Chem. Soc., 1994, 116, 9759; G. F. Mes, H. J. van Ramesdonk and J. W. Verhoeven, J. Am. Chem. Soc., 1984, 106, 1335; L. Fabbrizzi, M. Licchelli, P. Pallavicini and A. Taglietti, Inorg. Chem., 1996, 35, 1733.
21. R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy and K. R. A. S. Sandanayake, Top. Curr. Chem., 1993, 168, 223; A. W. Czarnik, Acc. Chem. Res., 1994, 27, 302; L. Fabbrizzi and A. Poggi, Chem. Soc. Rev., 1995, 24, 197; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281.
22. R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy and K. R. A. S. Sandanayake, Top. Curr. Chem., 1993, 168, 223; A. W. Czarnik, Acc. Chem. Res., 1994, 27, 302; L. Fabbrizzi and A. Poggi, Chem. Soc. Rev., 1995, 24, 197; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281.
23. R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy and K. R. A. S. Sandanayake, Top. Curr. Chem., 1993, 168, 223; A. W. Czarnik, Acc. Chem. Res., 1994, 27, 302; L. Fabbrizzi and A. Poggi, Chem. Soc. Rev., 1995, 24, 197; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281.
24. R. A. Bissell, A. P. de Silva, H. Q. N. Gunaratne, P. L. M. Lynch, G. E. M. Maguire, C. P. McCoy and K. R. A. S. Sandanayake, Top. Curr. Chem., 1993, 168, 223; A. W. Czarnik, Acc. Chem. Res., 1994, 27, 302; L. Fabbrizzi and A. Poggi, Chem. Soc. Rev., 1995, 24, 197; T. D. James, P. Linnane and S. Shinkai, Chem. Commun., 1996, 281.
25. See, for example, J. D. Ryder, Engineering Electronics, 2nd edn. McGraw-Hill, New York, 1967.
26. V. Balzani and F. Scandola, Supramolecular Photochemistry, Ellis-Horwood, Chichester, 1991; V. Balzani, A. Credi and F. Scandola, in Transition Metals in Supramolecular Chemistry, ed. L. Fabbrizzi and A. Poggi, Kluwer, Dordrecht, 1994, p. 1; J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
27. V. Balzani and F. Scandola, Supramolecular Photochemistry, Ellis-Horwood, Chichester, 1991; V. Balzani, A. Credi and F. Scandola, in Transition Metals in Supramolecular Chemistry, ed. L. Fabbrizzi and A. Poggi, Kluwer, Dordrecht, 1994, p. 1; J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
28. V. Balzani and F. Scandola, Supramolecular Photochemistry, Ellis-Horwood, Chichester, 1991; V. Balzani, A. Credi and F. Scandola, in Transition Metals in Supramolecular Chemistry, ed. L. Fabbrizzi and A. Poggi, Kluwer, Dordrecht, 1994, p. 1; J.-M. Lehn, Supramolecular Chemistry, VCH, Weinheim, 1995.
29. A. P. de Silva and R. A. D. D. Rupasinghe, J. Chem. Soc. Chem. Commun., 1985, 1669.
30. A. P. de Silva, H. Q. N. Gunaratne and P. L. M. Lynch, J. Chem. Soc., Perkin Trans. 2, 1995, 685; F. D. Saeva, J. Photochem. Photobiol. A: Chem., 1994, 78, 201.
31. A. P. de Silva, H. Q. N. Gunaratne and P. L. M. Lynch, J. Chem. Soc., Perkin Trans. 2, 1995, 685; F. D. Saeva, J. Photochem. Photobiol. A: Chem., 1994, 78, 201.
32. G. L. Closs and J. R. Miller, Science, 1988, 240, 440; M. N. Paddon-Row, Acc. Chem. Res., 1994, 27, 18.
33. G. L. Closs and J. R. Miller, Science, 1988, 240, 440; M. N. Paddon-Row, Acc. Chem. Res., 1994, 27, 18.
34. S. G. Schulman, R. Threatle, A. Capomacchia and W. Paul, J. Pharm. Sci., 1974, 63, 876.
35. F. Barigelletti, L. Flamigni, M. Guardigli, J.-P. Sauvage, J. P. Collin and A. Sour. Chem. Commun., 1996, 1329.
36. M. P. O'Neil, M. P. Niemczyk, W. A. Svec, D. Gosztola, G. L. Graines and M. R. Wasielewski, Science, 1992, 257, 63.
37. K. Connors, Binding Constants: The Measurement of Molecular Complex Stability, Wiley, New York, 1987.