Cu2+-induced blue shift of the pyrene excimer emission: A new signal transduction mode of pyrene probes

Organic Letters

Volumn 3, Issue 6, 2001, Pages 889-892

  Yang, Jye Shane ^a   Lin, Che Sheng ^a   Hwang, Chung Yu ^a  

^a NATIONAL CENTRAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001468285     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015524y     Document Type: Article

References (43)

1. Birks, J. B. Photophysics of Aromatic Molecules; Wiley-Interscience: London, 1970.
2. Winnik, F. M. Chem. Rev. 1993, 93, 587-614.
3. 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.
4. Selected examples of recently developed pyrene probes and sensors: (a) Lewis, F. D.; Zhang, Y.; Letsinger, R. L. J. Am. Chem. Soc. 1997, 119, 5451-5452.
5. (b) Lou, J.; Hatton, T. A.; Laibinis, P. E. Anal. Chem. 1997, 69, 1262-1264.
6. (c) Reis e Sousa, A. T.; Castanheira, E. M. S.; Fedorov, A. Martinho, J. M. G. J. Phys. Chem. A 1998, 102, 6406-6411
7. (d) Suzuki, Y.; Morozumi, T.; Nakamura, H.; Shimomura, M.; Hayashita, T.; Bartsh, R. A. J. Phys. Chem. B 1998, 102, 7910-7917.
8. (e) Monahan, C.; Bien, J. T.; Smith, B. D. Chem. Commun. 1998, 431-432.
9. (f) Matsui, J.; Mitsuishi, M.; Miyashita, T. Macromolecules 1999, 32, 381-386.
10. (g) Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463-9464.
11. (h) Principi, T.; Goh, C. C. E.; Liu, R. C. W.; Winnik, F. M. Macromolecules 2000, 33, 2958-2966.
12. (i) Sahoo, D.; Narayanaswami, V.; Kay, C. M.; Ryan, R. O. Biochemistry 2000, 39, 6594-6601.
13. (j) Krauss, R.; Weinig, H.-G.; Seydack, M.; Bendig, J.; Koert, U. Angew. Chem., Int. Ed. 2000, 39, 1835-1837.
14. Yang, J.-S.; Lee, C.-C.; Yau, S.-L.; Chang, C.-C.; Lee, C.-C.; Leu, J.-M. J. Org. Chem. 2000, 65, 871-877.
15. Yang, J.-S.; Liu, C.-P.; Lee, G.-H. Tetrahedron Lett. 2000, 41, 7911-7915.
16. (a) Yang, J.-S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 5321-5322.
17. (b) Yang, J.-S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864-11873.
18. Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
19. Akiyama, S.; Nakasuji, K.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 2231-2236.
20. 2+(acetate).
21. Connors, K. A. Binding Constants-The Measurement of Molecular Complex Stability; John Wiley & Sons: New York, 1987; Chapter 4.
22. Varnes, A. W.; Dodson, R. B.; Wehry, E. L. J. Am. Chem. Soc. 1972, 94, 946-950.
23. (a) Sasaki, D. Y.; Shnek, D. R.; Pack, D. W.; Arnold, F. H. Angew. Chem., Int. Ed. Engl. 1994, 34, 905-907.
24. (b) De Santis, G.; Fabbrizzi, L.; Licchelli, M.; Mangano, C.; Sacchi, D.; Sardone, N. Inorg. Chim. Acta 1997, 257, 69-76.
25. (c) Yoon, J.; Ohler, N. E.; Vance, D. H.; Aumiller, W. D.; Czarnik, A. W. Tetrahedron Lett. 1997, 38, 3845-3848.
26. (d) Torrado, A.; Walkup, G. K.; Imperiali, B. J. Am. Chem. Soc. 1998, 120, 609-610.
27. (e) Bolletta, F.; Costa, I.; Fabbrizzi, L.; Licchelli, M.; Montalti, M.; Pallavicini, P.; Prodi, L.; Zaccheroni, N. J. Chem. Soc., Dalton Trans. 1999, 1381-1385.
28. (f) Bodenant, B.; Weil, T.; Businelli-Pourcel, M.; Fages, F.; Barbe, B.; Pianet, I.; Laguerre, M. J. Org. Chem. 1999, 64, 7034-7039.
29. (g) Grandini, P.; Mancin, F.; Tecilla, P.; Scrimin, P.; Tonellato, U. Angew. Chem., Int. Ed. 1999, 38, 3061-3064.
30. Figures are shown as the Supporting Information.
31. 2 value (<1.10 in all cases), the randomness of the residuals, and the autocorrelation function.
32. 1 was used as the actinometer.
33. (a) De Schryver, F. C.; Collart, P.; Vandendriessche, J.; Goedeweeck, R.; Swinnen, A.; Van der Auweraer, M. Acc. Chem. Res. 1987, 20, 159-166.
34. (b) Matsui, A.; Mizuno, K.-I.; Tamai, N.; Yamazaki, I. Chem. Phys. 1987, 113, 111-117.
35. (c) Saigusa, H.; Lim, E. C. Acc. Chem. Res. 1996, 29, 171-178.
36. (d) Zimerman, O. E.; Weiss, R. G. J. Phys. Chem. A 1998, 102, 5364-5374.
37. (a) Ghosh, P.; Bharadwaj, P. K. J. Am. Chem. Soc. 1996, 118, 10579-10587.
38. (b) Ramachandram, B.; Samanta, A. J. Phys. Chem. A 1998, 102, 10579-10587.
39. (c) Mitchell, K. A.; Brown, R. G.; Yuan, D.; Chang, S.-C.; Utecht, R. E.; Lewis, D. E. J. Photochem. Photobiol. A: Chem. 1998, 115, 157-161.
40. (d) Rurack, K.; Kollmannsberger, M.; Resch-Genger, U.; Daub, J. J. Am. Chem. Soc. 2000, 122, 968-969.
41. 2+]/[1] ratios.
42. 2+.
43. The structures of 1 were optimized in the absence of metal ions using the MM2 force field supplied by Chem 3D Plus, a product of Cambridge Scientific Computing, Inc.