Design of a Hydrophobic Fluorescent Probe: An Amide-Linked Bispyrenyl Alcohol

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8565-8568

  Lewis, Frederick D ^a   Zhang, Yifan ^a   Letsinger, Robert L ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000837041     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971043+     Document Type: Article

References (31)

1. Winnik, F. M. Chem. Rev. (Washington, D.C.) 1993, 93, 587.
2. (a) Fages, F.; Bodenant, B.; Weil, T. J. Org. Chem. 1996, 61, 3956.
3. (b) Takeshita, M.; Shinkai, S. Chem. Lett. 1994, 125.
4. Kierzek, R.; Li, Y.; Turner, D. H.; Bevilacqua, P. C. J. Am. Chem. Soc. 1993, 115, 4985.
5. Bevilacqua, P. C.; Kierzek, R.; Johnson, K. A.; Turner, D. H. Science 1992, 258, 1355.
6. (e) Aoki, I.; Harada, T.; Sakaki, T.; Kawahara, Y.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1992, 1341.
7. (f) Aoki, I.; Kawabata, H.; Nakashima, K.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1991, 1771.
8. (g) Telser, J.; Cruickshank, K. A.; Morrison, L. E.; Netzel, T. L. J. Am. Chem. Soc. 1989, 111, 6966.
9. (a) Zachariasse, K. A.; Duveneck, G.; Kühnle, W.; Leinhos, U.; Reynders, P. In Photochemical Processes in Organized Molecular Systems; Honda, K., Ed.; Elsevier Science Publishers B.V.: Amsterdam, The Netherlands, 1991; p 83.
10. (b) Zachariasse, K. A.; Kühnle, W. Z. Phys. Chem. NF 1976, 101, 267.
11. Kühnle, W.; Zachariasse, K. A. J. Photochem. 1976, 5, 165.
12. Zachariasse, K. A.; Kühnle, W.; Weller, A. Chem. Phys. Lett. 1978, 59, 375.
13. Winnik, M. A.; Redpath, A. E. C.; Paton, K.; Danhelka, J. Polymer 1984, 25, 91.
14. (a) Lewis, F. D.; Wu, T.; Burch, E. L.; Bassani, D. M.; Yang, J.; Schneider, S.; Jäger, W.; Letsinger, R. L. J. Am. Chem. Soc. 1995, 117, 8785.
15. (b) Letsinger, R. L.; Wu, T. J. Am. Chem. Soc. 1994, 116, 811.
16. Lewis, F. D.; Zhang, Y.; Letsinger, R. L. Unpublished results.
17. Kitamura, M.; Nimura, A.; Yamana, K.; Shimidzu, T. Nucleic Acids Res. Symp. Ser. 1991, 25, 67.
18. Korshun, V. A.; Pestov, N. B.; Birikh, K. R.; Berlin, Y. A. Bioconjugate Chem. 1992, 3, 559.
19. For a recent example of the synthesis of amide-linked bispyrenes, see: Lou, J.; Hatton, T. A.; Laibinis, P. E. Anal. Chem. 1997, 69, 1262.
20. The synthesis of oligonucleotide conjugates of 3 and their use as fluorescent oligonucleotide probes have been reported; see: Lewis, F. D.; Zhang, Y.; Letsinger, R. L. J. Am. Chem. Soc. 1997, 119, 5451-5452.
21. Gaur, S. P.; Jain, P. C.; Anand, N. Indian J. Chem. 1982, 21B, 46.
22. Sinhababu, A. K.; Borchardt, R. T. Tetrahedron Lett. 1983, 24 227.
23. Winnik, F. M.; Tamai, N.; Yonezawa, Y.; Nishimura, Y.; Yamazaki, I. J. Phys. Chem. 1992, 96, 1967.
24. De Schryver, F. C.; Collart, P.; Vandendriessche, J.; Goedeweeck, R.; Swinnen, A.; Van der Auweraer, M. Acc. Chem. Res. 1987, 20, 159.
25. Paliwal, S.; Geib, S.; Wilcox, C. S. J. Am. Chem. Soc. 1994, 116, 4497.
26. Newcomb, L. F.; Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 6509.
27. Warschel, A.; Huler, E. Chem. Phys. 1974, 6, 463.
28. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
29. Stevens, B. Spectrochem. Acta 1962, 18, 439.
30. Binovi, L. J.; Arit, H. G., Jr. J. Org. Chem. 1961, 26, 1656.
31. Aoki, I.; Kawahara, Y.; Sakaki, T.; Harada, T.; Shinkai, S. Bull. Chem. Soc. Jpn. 1993, 66, 927.