Proton-induced fluorescence switching in novel naphthalimide-dansylamide dyads

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10565-10568

  Abad, Sergio ^a   Kluciar, Marek ^b   Miranda, Miguel A ^a   Pischel, Uwe ^b  

^a CSIC   (Spain)

^b UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSITIONS; ENERGY TRANSFER; FLUORESCENCE; OPTICAL SWITCHES; REACTION KINETICS; SPECTRUM ANALYSIS;

DYADS; ELECTRON TRANSFER; MOLECULAR OPTICAL SWITCH; PROTON-INDUCED FLUORESCENCE;

PROTONS;

1,8 NAPHTHALIMIDE; ACETONITRILE; COUMARIN; DANSYL AMIDE; FLUORESCENT DYE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; FLUORESCENCE RESONANCE ENERGY TRANSFER; PHOTOLYSIS; PROTON TRANSPORT; QUANTUM YIELD; REDUCTION; TEMPERATURE DEPENDENCE; THERMODYNAMICS; TITRIMETRY;

EID: 28744444902     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0512195     Document Type: Article

References (38)

1. (a) 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.
2. (b) Martínez-Máñez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419-4476.
3. (c) Prodi, L. New J. Chem. 2005, 29, 20-31.
4. See, for example: (a) Choi, M.; Kim, M.; Lee, K. D.; Han, K.-N.; Yoon, I.-A.; Chung, H.-J.; Yoon, J. Org. Lett. 2001, 3, 3455-3457.
5. (b) Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Lett. 2002, 4, 2449-2452.
6. (c) Bu, J.-H.; Zheng, Q.-Y.; Chen, C.-F.; Huang, Z.-T. Org. Lett. 2004, 6, 3301-3303.
7. (d) Pina, F.; Maestri, M.; Balzani, V.; Vögtle, F. ChemPhysChem 2004, 5, 473-480.
8. (e) Hanaoka, K.; Kikuchi, K.; Kojima, H.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2004, 126, 12470-12476.
9. Benniston, A. C. Ckem. Soc. Rev. 2004, 33, 573-578.
10. Armaroli, N.; Eckert, J.-F.; Nierengarten, J.-F. Chem. Commun. 2000, 2105-2106.
11. Serroni, S.; Campagna, S.; Pistone Nascone, R.; Hanan, G. S.; Davidson, G. J. E.; Lehn, J.-M. Chem. Eur. J. 1999, 5, 3523-3527.
12. Cárdenas, D. J.; Collin, J.-P.; Gavina, P.; Sauvage, J.-P.; De Cian, A.; Fischer, J.; Armaroli, N.; Flamigni, L.; Vicinelli, V.; Balzani, V. J. Am. Chem. Soc. 1999, 121, 5481-5488.
13. Akasaka, T.; Mutai, T.; Otsuki, J.; Araki, K. J. Chem. Soc., Dalton Trans. 2003, 1537-1544.
14. Suppan, P.; Ghoneim, N. Solvatochromism; The Royal Chemical Society: Cambridge, 1997.
15. See, for example: (a) Walkup, G. K.; Imperial., B. J. Am. Chem. Soc. 1997, 119, 3443-3450.
16. (b) Prodi, L.; Boletta, F.; Montalti, M.; Zaccheroni, N. Eur. J. Inorg. Chem. 1999, 455-460.
17. (c) Vögtle, F.; Gestermann, S.; Kauffmann, C.; Ceroni, P.; Vicinelli, V.; Balzani, V. J. Am. Chem. Soc. 2000, 122, 10398-10404.
18. (d) Montalti, M.; Prodi, L.; Zaccheroni, N.; Falini, G. J. Am. Chem. Soc. 2002, 124, 13540-13546.
19. (e) Vicinelli, V.; Ceroni, P.; Maestri, M.; Balzani, V.; Gorka, M.; Vögtle, F. J. Am. Chem. Soc. 2002, 124, 6461-6468.
20. (f) Jiang, P.; Chen, L.; Lin, J.; Liu, Q.; Ding, J.; Gao, X.; Guo, Z. Chem. Commun. 2002, 1424-1425.
21. (g) Zheng, Y.; Gattás-Asfura, K. M.; Konka, V.; Leblanc, R. M. Chem. Commun. 2002, 2350-2351.
22. (h) Métivier, R.; Leray, I.; Valeur, B. Chem. Commun. 2003, 996-997.
23. (i) Métivier, R.; Leray, I; Valeur, B. Photochem. Photobiol. Sci. 2004, 3, 374-380.
24. See, for example: (a) Daffy, L. M.; de Silva, A. P.; Gunaratne, H. Q. N.; Huber, C.; Lynch, P. L. M.; Werner, T.; Wolfbeis, O. S. Chem. Eur. J. 1998, 4, 1810-1815.
25. (b) Ramachandram, B.; Saroja, G.; Sankaran, N. B.; Samanta, A. J. Phys. Chem. B 2000, 104, 11824-11832.
26. (c) Gunnlaugsson, T.; Clive Lee, T.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265-3267.
27. (d) Licchelli, M.; Orbelli Biroli, A.; Poggi, A.; Sacchi, D.; Sangermani, C.; Zema, M. J. Chem. Soc., Dalton Trans. 2003, 4537-4545.
28. (a) Wintgens, V.; Valat, P.; Kossanyi, J.; Biczok, L.; Demeter, A.; Bérces, T. J. Chem. Soc., Faraday Trans. 1994, 90, 411-421.
29. (b) Jones, G., II; Kumar, S. J. Photochem. Photobiol. A 2003, 160, 139-149.
30. Ceroni, P.; Laghi, I.; Maestri, M.; Balzani, V.; Gestermann, S.; Gorka, M.; Vögtle, F. New. J. Chem. 2002, 26, 66-75.
31. 00(NAPIM) = 3.51 eV (cf. ref 11b). The coulomb term C was taken as -0.06 eV.
32. Speiser, S. Chem. Rev. 1996, 96, 1953-1976.
33. -1).
34. The experimental determination of accurate rate constants for PET and SSET quenching of singlet-excited NAPIM by DANS in the dyads is complicated by the short fluorescence lifetime of the imide chromophore [0.145 ns for N-methy-1,8-naphthalimide (cf. ref 11a)].
35. (a) Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753.
36. (b) Alderighi, L.; Gans, P.; Ienco, A.; Peters, D.; Sabatini, A.; Vacca, A. Coord. Chem. Rev. 1999, 184, 311-318.
37. Valeur, B.; Pouget, J.; Bourson, J.; Kaschke, M.; Ernsting, N. P. J. Phys. Chem. 1992, 96, 6545-6549. For other examples, see also ref 1a.
38. Raymo, F. M.; Giordani, S. J. Am. Chem. Soc. 2002, 124, 2004-2007.