Evaluation of a simple and novel fluorescent anion sensor, 4-quinolone, and modification of the emission color by substitutions based on molecular orbital calculations

Tetrahedron

Volumn 62, Issue 43, 2006, Pages 10065-10071

  Hirano, Junzo ^a   Hamase, Kenji ^a   Zaitsu, Kiyoshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

4 Quinolone; Anion sensor; Fluorescence; Intramolecular charge transfer; Molecular orbital calculation

Indexed keywords

4 QUINOLONE DERIVATIVE; ANION;

AB INITIO CALCULATION; ARTICLE; BINDING AFFINITY; CALCULATION; COLOR; ENERGY; EVALUATION; FLUORESCENCE; PRIORITY JOURNAL; QUANTUM CHEMISTRY; SENSOR;

EID: 33748421870     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.060     Document Type: Article

References (42)

1. Martinez-Manez R., and Sancenon F. Chem. Rev. 103 (2003) 4419-4476
2. Gale P.A. Coord. Chem. Rev. 240 (2003) 191-221
3. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486-516
4. Kang J., Kim H.S., and Jang D.O. Tetrahedron Lett. 46 (2005) 6079-6082
5. Gunnlaugsson T., Davis A.P., Hussey G.M., Tierney J., and Glynn M. Org. Biomol. Chem. 2 (2004) 1856-1863
6. Gunnlaugsson T., Davis A.P., O'Brien J.E., and Glynn M. Org. Lett. 4 (2002) 2449-2452
7. Kim S.K., and Yoon J. Chem. Commun. (2002) 770-771
8. Gunnlaugsson T., Davis A.P., and Glynn M. Chem. Commun. (2001) 2556-2557
9. Vance D.H., and Czarnik A.W. J. Am. Chem. Soc. 116 (1994) 9397-9398
10. Aldakov D., Palacios M.A., and Anzenbacher Jr. P. Chem. Mater. 17 (2005) 5238-5241
11. Curiel D., Cowley A., and Beer P.D. Chem. Commun. (2005) 236-238
12. Wen Z.-C., and Jiang Y.-B. Tetrahedron 60 (2004) 11109-11115
13. Kovalchuk A., Bricks J.L., Reck G., Rurack K., Schulz B., Szumna A., and Weibhoff H. Chem. Commun. (2004) 1946-1947
14. Pohl R., Aldakov D., Kubat P., Jursikova K., Marquez M., and Anzenbacher Jr. P. Chem. Commun. (2004) 1282-1283
15. Xu G., and Tarr M.A. Chem. Commun. (2004) 1050-1051
16. Aldakov D., and Anzenbacher Jr. P. Chem. Commun. (2003) 1394-1395
17. Wu F.-Y., and Jiang Y.-B. Chem. Phys. Lett. 355 (2002) 438-444
18. Black C.B., Andrioletti B., Try A.C., Ruiperez C., and Sessler J.L. J. Am. Chem. Soc. 121 (1999) 10438-10439
19. Zhang X., Guo L., Wu F.-Y., and Jiang Y.-B. Org. Lett. 5 (2003) 2667-2670
20. Choi K., and Hamilton A.D. Angew. Chem., Int. Ed. 40 (2001) 3912-3915
21. Beer P.D. Acc. Chem. Res. 31 (1998) 71-80
22. Wu J.-S., Zhou J.-H., Wang P.-F., Zhang X.-H., and Wu S.-K. Org. Lett. 7 (2005) 2133-2136
23. Nishizawa S., Kato Y., and Teramae N. J. Am. Chem. Soc. 121 (1999) 9463-9464
24. Nishizawa S., Kaneda H., Uchida T., and Teramae N. J. Chem. Soc., Perkin Trans. 2 (1998) 2325-2327
25. Fabbrizzi L., Marcotte N., Stomeo F., and Taglietti A. Angew. Chem., Int. Ed. 41 (2002) 3811-3814
26. Wiskur S.L., Ait-Haddou H., Lavigne J.J., and Anslyn E.V. Acc. Chem. Res. 34 (2001) 963-972
27. Metzger A., and Anslyn E.V. Angew. Chem., Int. Ed. 37 (1998) 649-652
28. Niikura K., Metzger A., and Anslyn E.V. J. Am. Chem. Soc. 120 (1998) 8533-8534
29. Hirano J., Hamase K., Fukuda H., Tomita T., and Zaitsu K. J. Chromatogr., A 1059 (2004) 225-231
30. Hirano J., Hamase K., Akita T., and Zaitsu K. Anal. Sci. 21 (2005) x45-x46
31. Wilson J.N., and Bunz U.H.F. J. Am. Chem. Soc. 127 (2005) 4124-4125
32. Urano Y., Kamiya M., Kanda K., Ueno T., Hirose K., and Nagano T. J. Am. Chem. Soc. 127 (2005) 4888-4894
33. Gabe Y., Urano Y., Kikuchi K., Kojima H., and Nagano T. J. Am. Chem. Soc. 126 (2004) 3357-3367
34. Shevyakov S.V., Li H., Muthyala R., Asato A.E., Croney J.C., Jameson D.M., and Liu R.S.H. J. Phys. Chem. A 107 (2003) 3295-3299
35. Yamaguchi S., Shirasaka T., Akiyama S., and Tamao K. J. Am. Chem. Soc. 124 (2002) 8816-8817
36. Gould Jr. R.G., and Jacobs W.A. J. Am. Chem. Soc. 61 (1939) 2890-2895
37. Castioni N.V., Baehni P.C., and Gurny R. Eur. J. Pharm. Biopharm. 45 (1998) 101-111
38. Kanis J.A., and Sheffield M.D. Am. J. Med. 95 (1993) S53-S61
39. Rose N.J., and Drago R.S. J. Am. Chem. Soc. 81 (1959) 6138-6141
40. Leyva E., Monreal E., and Hernandez A. J. Fluorine Chem. 94 (1999) 7-10
41. Koga H., Itoh A., Murayama S., Suzue S., and Irikura T. J. Med. Chem. 23 (1980) 1358-1363
42. Lin A.J., and Loo T.L. J. Med. Chem. 21 (1978) 268-272