Intramolecular fluorescence quenching of crowned 7-aminocoumarins as potential fluorescent chemosensors

Journal of Fluorescence

Volumn 14, Issue 2, 2004, Pages 193-202

  Rusalov, Michael V ^a   Druzhinin, Sergey I ^a   Uzhinov, Boris M ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

7 aminocoumarins; Complex formation; Crown ethers; Electron transfer; Fluorescence quenching; Fluorescent chemosensors

Indexed keywords

ABSORPTION SPECTROSCOPY; AMINES; CHEMICAL SENSORS; COMPLEXATION; DENSITY (OPTICAL); DERIVATIVES; ETHERS; FLUOROMETERS; METHANOL; QUENCHING; SOLVENTS; VISCOSITY;

7-AMINOCOUMARINS; COMPLEX FORMATION; CROWN-ETHERS; ELECTRON TRANSFER; FLUORESCENCE QUENCHING; FLUORESCENT CHEMOSENSORS;

FLUORESCENCE;

7 AMINOCOUMARIN; 7-AMINOCOUMARIN; COUMARIN DERIVATIVE; CROWN COMPOUND; FLUORESCENT DYE;

ARTICLE; CHEMISTRY; FLUORESCENCE; PHOTOCHEMISTRY; SYNTHESIS;

COUMARINS; CROWN COMPOUNDS; FLUORESCENCE; FLUORESCENT DYES; PHOTOCHEMISTRY;

EID: 3543147277     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:JOFL.0000016291.26652.3b     Document Type: Conference Paper

References (38)

1. F. Vögtle and E. Weber (Ed.) (1985). Host Guest Complex Chemistry Macrocycles: Synthesis, Structures, Applications, Springer-Verlag, Berlin.
2. A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, and T. E. Rice (1997). Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97(5), 1515-1566.
3. H.-G. Löhr and F. Vögtle (1985). Chromo- and fluoroionophores. A new class of dye reagents. Acc. Chem. Res. 18, 65-72.
4. A. P. de Silva and S. A. de Silva (1986). Fluorescent signalling crown ethers. 'Switching On' of fluorescence by alkali metal ion recognition and binding in situ. J. Chem. Soc., Chem. Commun. 1709-1710.
5. J. Bourson, J. Pouget, and B. Valeur (1993). Ion-responsive fluorescent compounds. 4. Effect of cation binding on the photophysical properties of a coumarin linked to monoaza- and diaza-crown ethers. J. Phys. Chem. 97(17), 4552-4557.
6. J. Bourson, M.-N. Borrel, and B. Valeur (1992). Ion-responsive fluorescent compounds. Part 3. Cation complexation with coumarin 153 linked to monoaza-15-crown-5. Anal. Chim. Acta 257, 189-193.
7. J. R. Lakowicz (1983). Principles of Fluorescence Spectroscopy, Plenum Press, New York.
8. W. H. Melhuish (1961). Quantum efficiencies of fluorescence of organic substances-effect of solvent and concentration of fluorescent solute. J. Phys. Chem. 65(2), 229-235.
9. V. L. Lapteva, M. V. Rusalov, V. V. Samoshin, M. A. Kirpichenok, S. I. Druzhinin, B. M. Uzhinov, and N. S. Zefirov (1995). New coumarin-containing fluoroionophores. Doklady Chem. 344(1-3), 202-204.
10. A. Weissberger, E. S. Proskauer, J. A. Riddick, and E. E. Toops (1955). Organic Solvents. Physical Properties and Methods of Purification. Interscience Publishers, New York.
11. N. A. Nemkovich, H. Reis, and W. Baumann (1997). Ground and excited state dipole moments of coumarin laser dyes: Investigation by electro-optical absorption and emission methods. J. Lumin. 71, 255-263.
12. E. Lippen (1955). Dipolmoment und Elektronenstruktur von Angeregten Molekülen, Z. Naturforsch. A 10(7), 541-545.
13. W. Rettig and A. Klock (1985). Intramolecular fluorescence quenching in aminocoumarines - identification of an excited-state with full charge separation. Can. J. Chem. 63(7), 1649-1653.
14. S. I. Druzhinin, B. D. Bursulaya, and B. M. Uzhinov (1991). Charged substituents and the effect of their electric-field on the electronic-spectra of some aminocoumarins. Chem. Phys. 158(1), 137-142.
15. A. F. Clifford et al. (Eds.) (1964). International Encyclopedia of Chemical Science, D. Van Nostrand Company, Toronto.
16. J.-L. Habib-Jiwan, C. Branger, J.-Ph. Soumillion, and B. Valeur (1998). Ion-responsive fluorescent compounds V. Photophysical and complexing properties of coumarin 343 linked to monoaza-15-crown-5. J. Photochem. Photobiol. A: Chem. 116, 127-133.
17. G. Jones II, W. R. Jackson, and A. M. Halpern (1980). Medium effects on fluorescence quantum yields and lifetimes for coumarin laser dyes. Chem. Phys. Lett. 72(2), 391-395.
18. Chao-Tsen Chen and Wan-Pei Huang (2002). A highly selective fluorescent chemosensor for lead ions. J. Am. Chem. Soc. 124, 6246-6247.
19. G. Jones II, S. F. Griffin, Ch. Choi, and W. R. Bergmark (1984). Electron donor-acceptor quenching and photoinduced electron transfer for coumarin dyes. J. Org. Chem. 49, 2705-2708.
20. S. Nad and H. Pal (2000). Electron transfer from aromatic amines to excited coumarin dyes: Fluorescence quenching and picosecond transient absorption studies. J. Phys. Chem. A 104(3), 673-680.
21. S. Nad and H. Pal (2000). Electron transfer from diphenyl and triphenyl amines to excited coumarin dyes. J. Photochem. Photobiolog. A: Chem. 134, 9-15.
22. R. A. Beecroft, R. S. Davidson, D. Goodwin, J. E. Pratt, and X. J. Luo (1986). Quenching of the triplet states of aromatic hydrocarbons by tertiary amines. J. Chem. Soc., Faraday Trans. 2 82, 2393-2397.
23. C. A. Parker (1968). Photoluminescence of Solutions, Elsevier, Amsterdam.
24. D. F. Othmer and M. S. Thakar (1953). Correlating diffusion coefficients in liquids. Ind. Eng. Chem. 45(3), 589-593.
25. A. Demeter, S. Druzhinin, M. George, E. Haselbach, J.-L. Roulin, and K. A. Zachariasse (2000). Dual fluorescence and fast intramolecular charge transfer with 4-(diisopropylamino) benzonitrile in alkane solvents. Chem. Phys. Lett. 323(3-4), 351-360.
26. S. I. Druzhinin and B. M. Uzhinov (1982). Proton transfer and nonradiative deactivation in excited ion pairs of N,N-dimethyl-1-naphthylamine with carboxylic acids. Theor. Exp. Chem. 18(5), 515-522.
27. R. C. Reid, J. M. Prausnitz, and Th. K. Sherwood (1977). The Properties of Gases and Liquids, McGraw-Hill, New York.
28. S. I. Druzhinin, Y.-B. Jiang, A. Demeter, and K. A. Zachariasse (2001). Internal conversion with 4-(azetidinyl)benzonitriles in alkane solvents. Influence of fluoro substitution. Phys. Chem. Chem. Phys. 3(23), 5213-5221.
29. S. I. Druzhinin, A. Demeter, V. A. Galievsky, T. Yoshihara, and K. A. Zachariasse (2003). Thermally activated internal conversion with 4-(dimethylamino)benzonitrile, 4-(methylamino) benzonitrile, and 4-aminobenzonitrile in alkane solvents. No correlation with intramolecular charge transfer. J. Phys. Chem. A 107(40), 8075-8085.
30. I. Rückert, A. Demeter, O. Morawski, W. Kuhnle, E. Tauer, and K. A. Zachariasse (1999). Internal conversion in 1-aminonaphthalenes. Influence of amino twist angle. J. Phys. Chem. A 103(13), 1958-1966.
31. D. Rehm and A. Weller (1970). Kinetics of fluorescence quenching by electron and H-atom transfer. Isr. J. Chem. 8(2), 259-272.
32. C. A. M. Seidel, A. Schulz, and M. H. M. Sauer (1996). Nucleobase-specific quenching of fluorescent dyes. 1. Nucleobase one-electron redox potentials and their correlation with static and dynamic quenching efficiencies. J. Phys. Chem. 100(13), 5541-5553.
33. K. I. Priyadarsini and J. P. Mittal (1991). Effect of 1,4-diazabicyclo-[2,2,2]-octane on the laser properties of 7-amino coumarin dyes. J. Photochem. Photobiolog. A: Chem. 61(3), 381-388.
34. S. S. Jayanthi and P. Ramamurthy (1998). Excited singlet state reaction of phenosafranine with electron donors. Role of the heavy-atom effect in triplet induction. J. Chem. Soc., Faraday Trans. 94(12), 1675-1679.
35. Yu. Nagasawa, A. P. Yartsev, K. Tominaga, A. E. Johnson, and K. Yoshihara (1993). Substituent effects on intermolecular electron transfer: Coumarins in electron-donating solvents. J. Am. Chem. Soc. 115(17), 7922-7923.
36. Ch. Wang, B. Akhremitchev, and G. C. Walker (1997). Femtosecond infrared and visible spectroscopy of photoinduced intermolecular' electron transfer dynamics and solvent-solute reaction geometries: Coumarin 337 in dimethylaniline. J. Phys. Chem. A 101(15), 2735-2738.
37. H. Shirota, H. Pal, K. Tominaga, and K. Yoshihara (1998). Ultrafast intermolecular electron transfer in coumarin-hydrazine system. Chem. Phys. 236, 355-364.
38. n-(N,N- dimethylaniline) systems. Chem. Phys. Lett. 14(5), 563-568.