2-Aryl-3-hydroxyquinolones, a new class of dyes with solvent dependent dual emission due to excited state intramolecular proton transfer

New Journal of Chemistry

Volumn 30, Issue 5, 2006, Pages 774-781

  Yushchenko, Dmytro A ^a,b   Shvadchak, Volodymyr V ^b   Klymchenko, Andrey S ^b   Duportail, Guy ^b   Mély, Yves ^b   Pivovarenko, Vasyl G ^a  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 2 (4 FLUOROPHENYL) 3 HYDROXY 4(1H) QUINOLONE; 1 METHYL 2 (4 METHOXYPHENYL) 3 HYDROXY 4(1H) QUINOLONE; 1 METHYL 2 (4 METHYLPHENYL) 3 HYDROXY 4(1H) QUINOLONE; 1 METHYL 2 PHENYL 3 HYDROXY 4(1H) QUINOLONE; 1 METHYL 2 [4 (TRIFLUOROMETHYL)PHENYL] 3 HYDROXY 4(1H) QUINOLONE; 2 (2 THIENYL) 3 HYDROXY 4(1H) QUINOLONE; 2 PHENYL 3 HYDROXY 4(1H) QUINOLONE; 3 HYDROXYFLAVONE; 3 QUINOLINOL DERIVATIVE; FLUORESCENT DYE; HETEROCYCLIC NITRO COMPOUND; METHYL GROUP; ORGANIC SOLVENT; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINOLINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; ENTROPY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; LIGHT ABSORPTION; PKA; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM CHEMISTRY; QUANTUM YIELD; STEADY STATE;

EID: 33646594106     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/b601400c     Document Type: Article

References (45)

1. G. R Bright G. W. Fisher J. Rogowska D. L. Taylor Methods Cell Biol. 1989 30 157 192
2. Z. R. Grabowski K. Rotkiewicz W. Rettig Chem. Rev. 2003 103 3899 4031
3. S. J. Formosinho L. G. Arnaut J. Photochem. Photobiol., A 1993 75 21 48
4. D. Le Gourrierec S. M. Ormson R. G. Brown Prog. React. Kinet. 1994 19 211 275
5. T. C. Swinney D. F. Kelley J. Chem. Phys. 1993 99 211 221
6. A. S. Klymchenko T. Ozturk V. G. Pivovarenko A. P. Demchenko Can. J. Chem. 2001 79 358 363
7. A. S. Klymchenko T. Ozturk V. G. Pivovarenko A. P. Demchenko Tetrahedron Lett. 2001 42 7967 7970
8. A. S. Klymchenko T. Ozturk A. P. Demchenko Tetrahedron Lett. 2002 43 7079 7082
9. A. S. Klymchenko T. Ozturk V. G. Pivovarenko A. P. Demchenko New J. Chem. 2003 27 1336 1343
10. S. Ercelen A. S. Klymchenko A. P. Demchenko Anal. Chim. Acta 2002 464 273 287
11. A. S. Klymchenko V. G. Pivovarenko A. P. Demchenko J. Phys. Chem. A 2003 107 4211 4216
12. A. S. Klymchenko A. P. Demchenko Phys. Chem. Chem. Phys. 2003 5 461 468
13. A. S. Klymchenko G. Duportail T. Ozturk Y. Mély A. P. Demchenko Proc. Natl. Acad. Sci. USA 2003 100 11219 11224
14. O. P. Bondar V. G. Pivovarenko E. S. Rowe Biochim. Biophys. Acta 1998 1369 119 130
15. S. M. Dennison J. Guharay P. K. Sengupta Spectrochim. Acta, Part A 1999 55 1127 1132
16. V. V. Shynkar A. S. Klymchenko G. Duportail A. P. Demchenko Y. Mely Biochim. Biophys. Acta 2005 1712 128 136
17. S. Ercelen A. S. Klymchenko A. P. Demchenko FEBS Lett. 2003 538 25 28
18. A. S. Klymchenko S. V. Avilov A. P. Demchenko Anal. Biochem. 2004 329 43 57
19. A. Sytnik D. Gormin M. Kasha Proc. Natl. Acad. Sci. USA 1994 91 11968 11972
20. D. Roshal A. V. Grigorovich A. O. Doroshenko V. G. Pivovarenko A. P. Demchenko J. Phys. Chem. 1998 102 5907 5914
21. X. Poteau G. Saroja C. Spies R. G. Brown J. Photochem. Photobiol., A 2004 162 431 439
22. V. G. Pivovarenko O. B. Vadzyuk S. O. Kosterin J. Fluoresc. 2006 10.1007/s10895-005-0020-5
23. D. A. Yushchenko M. D. Bilokin O. V. Pyvovarenko G. Duportail Y. Mely V. G. Pivovarenko Tetrahedron Lett. 2006 47 905 908
24. F. Gao K. F. Johnson J. B. Schlenoff J. Chem. Soc., Perkin Trans. 2 1996 2 269 273
25. V. V. Shynkar Y. Mély G. Duportail E. Piémont A. S. Klymchenko A. P. Demchenko J. Phys. Chem. A 2003 107 9522 9529
26. A. D. Roshal J. A. Organero A. Douhal Chem. Phys. Lett. 2003 379 53 59
27. K. Livesey J.-C. Brochon Biophys. J. 1987 52 693 706
28. J.-C. Brochon Methods Enzymol. 1994 240 262 311
29. A. O. Doroshenko L. B. Sychevskaya A. V. Grygorovych V. G. Pivovarenko J. Fluoresc. 2002 12 455 464
30. D. M. Himmelblau, Applied Nonlinear Programming, McGraw-Hill Book Company, 1972 (Russian edn, Moscow, Mir, 1975)
31. I. J. Berstein and Y. L. Kaminskij, Spectrophotometric Analysis in Organic Chemistry, Khimija, Leningrad, 1986
32. K. D. Belfield M. V. Bondar Y. Liu O. V. Przhonska J. Phys. Org. Chem. 2003 16 69 78
33. J. R. Lakovicz, Principles of Fluorescence Spectroscopy, Kluwer Academic/Plenum Publishers, New York, 2nd edn, 1999, p. 52
34. M. J. S. Dewar E. G. Zoebich E. F. Healy J. P. Stewart J. Am. Chem. Soc. 1985 107 3902 3908
35. P. Hradil J. Jirman Collect. Czech. Chem. Commun. 1995 60 1357 1366
36. S. Ozbei E. Kendi G. K. Ayhan R. Eltan Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1999 55 678 680
37. G. Smith J. P. Bartley E. Wang R. C. Bott Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2001 57 1336 1337
38. I. Lippai G. Speier J. Huttner L. Zsolnai Acta Crysallogr., Sect. C: Cryst. Struct. Commun. 1997 53 1547 1549
39. P. Hradil P. Krejci J. Hlavac I. Wiedermannova A. Lycka V. Bertolasi J. Heterocycl. Chem. 2004 41 375
40. A. S. Klymchenko A. P. Demchenko New J. Chem. 2004 28 687 692
41. W. R. Laws L. Brand J. Phys. Chem. 1979 83 795 802
42. A. S. Klymchenko V. G. Pivovarenko A. P. Demchenko Spectrochim. Acta, Part A 2003 59 787 792
43. A. J. G. Strandjord D. E. Smith P. F. Barbara J. Phys. Chem. 1985 89 2362
44. F. A. Carey and R. J. Sundberg, Advanced Organic Chemistry, Part A, Kluwer Academic/Plenum Publishers, New York, 4th edn, 2000, pp. 204-215
45. J. Catalan V. Lopez P. Pçerez R. Martin-Villamil J. G. Rodriguez Liebigs Ann. 1995 241