Abstract
3-Hydroxychromones (3HC), exhibit dual emissions highly sensitive to solvent properties due to excited state intramolecular proton transfer (ESIPT). Therefore, 3HCs find wide applications as fluorescence probes in biological systems. Here, it is particularly important to understand the fluorescence behaviour of 3HCs in polar environments. Herein, we studied 3-hydroxyflavone, 2-(2-furyl)-3-hydroxychromone and 2-(2-benzofuryl)-3-hydroxychromone in high polarity solvents characterized by different H-bond donor abilities, donor concentrations and acceptor abilities. Our results show that the dual emissions of the dyes are insensitive to solvent basicity but strongly depend on the two other parameters. Moreover, furyl-and benzofuryl-substituted dyes were significantly more sensitive than the 3-hydroxyflavone to H-bond donor ability, while all three dyes showed roughly equivalent high sensitivity to H-bond donor concentration. These results can be explained by different mechanisms. Thus, the sensitivity of all three dyes to increasing concentrations of H-bond donors probably results from increase in the population of solvated dye with disrupted intramolecular H-bonds. Meantime, the sensitivity to H-bond donor ability of the solvent, observed mainly with furyl and benzofuryl dyes, is probably related to the strength of the H-bonds between the solvent and the 4-carbonyl group of the dye with intact intramolecular H-bonds. The present results provide new insights for further applications of 3HC derivatives as environment-sensitive probes and labels of biological molecules.
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References
Sengupta P K and Kasha M 1979 Chem. Phys. Lett. 68 382
Klymchenko A S and Demchenko A P 2003 Phys. Chem. Chem. Phys. 5 461
Bright G R, Fisher G W, Rogowska J and Taylor D L 1989 Methods Cell Biol. 30 157
Silver R B 1998 Methods Cell Biol. 56 237
Ercelen S, Klymchenko A S and Demchenko A P 2002 Anal. Chim. Acta 464 273
Liu W, Wang Y, Jin W, Shen G and Yu R 1999 Anal. Chim. Acta 383 299
Roshal A D, Grigorovich A V, Doroshenko A O, Pivovarenko V G and Demchenko A P 1998 J. Phys. Chem. A102 5907
Klymchenko A S and Demchenko A P 2002 J. Am. Chem. Soc. 124 12372
Klymchenko A S, Duportail G, Mély Y and Demchenko A P 2003 Proc. Natl. Acad. Sci. USA 100 11219
Dharia J R, Johnson K F and Schlenoff J B 1994 Macromolecules 27 5167
Dennison S M, Guharay J and Sengupta P K 1999 Spectrochim. Acta A55 1127
Klymchenko A S and Demchenko A P 2002 Langmuir 18 5637
Tormo L and Douhal A 2005 J. Photochem. Photobiol. A173 358
Bondar O P, Pivovarenko V G and Rowe E S 1998 Biochim. Biophys. Acta 1369 119
Klymchenko A S, Duportail G, Oztürk T, Pivovarenko V G, Mély Y and Demchenko A P 2002 Chem. Biol. 9 1199
Klymchenko A S, Duportail G, Demchenko A P and Mély Y 2004 Biophys. J. 86 2929
Klymchenko A S, Mély Y, Demchenko A P and Duportail G 2004 Biochim. Biophys. Acta 1665 6
Shynkar V V, Klymchenko A S, Duportail G, Demchenko A P and Mély Y 2005 Biochim. Biophys. Acta 1712 128
Ercelen S, Klymchenko A S and Demchenko A P 2003 FEBS Lett. 538 25
Klymchenko A S, Avilov S V and Demchenko A P 2004 Anal. Biochem. 329 43
Avilov S V, Bode C, Tolgyesi F G, Klymchenko A S, Fidy J and Demchenko A P 2005 Int. J. Biol. Macromol. 36 290
Guharay J, Sengupta B and Sengupta P K 2001 Proteins: Struct., Function Genet. 43 75
Sytnik A, Gormin D and Kasha M 1994 Proc. Natl. Acad. Sci. USA 91 11968
Klymchenko A S, Pivovarenko V G, Oztürk T and Demchenko A P 2003 New J. Chem. 27 1336
Klymchenko A S and Demchenko A P 2004 New J. Chem. 28 687
Reichardt C 1994 Chem. Rev. 94 2319
Strandjord A J G and Barbara P F 1985 J. Phys. Chem. 89 2355
Swinney T C and Kelley F D 1993 J. Chem. Phys. 99 211
McMorrow D and Kasha M 1984 J. Phys. Chem. 88 2235
Klymchenko A S, Pivovarenko V G, and Demchenko A P 2003 Spectrochim. Acta A59 787
Abraham M H 1993 J. Phys. Org. Chem. 6 660
Abraham M H, Chadha H S, Whiting G S and Mitchell R C 1994 J. Pharm. Sci. 83 1085
Ormson, S M, Brown R G, Volmer F Rettig J 1994 J. Photochem. Photobiol. A81 65
Ameer-Beg S, Ormson S M, Brown R G, Matousek P, Towrie M, Nibbering E T J, Foggi P and Neuwahl F V R 2001 J. Phys. Chem. A105 3709
Strandjord A J G and Barbara P F 1984 J. Phys. Chem. 89 2355
Woolfe G J and Thistlethwaite P J 1981 J. Am. Chem. Soc. 103 6916
Klymchenko A S, Pivovarenko V G and Demchenko A P 2003 J. Phys. Chem. A107 4211
Shynkar V V, Klymchenko A S, Piemont E, Demchenko A P and Mely Y 2004 J Phys. Chem. A108 8151
Yesylevskyy S O, Klymchenko A S and Demchenko A P 2005 J. Mol. Struct. (Theochem.) 755 229
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Klymchenko, A.S., Kenfack, C., Duportail, G. et al. Effects of polar protic solvents on dual emissions of 3-hydroxychromones. J Chem Sci 119, 83–89 (2007). https://doi.org/10.1007/s12039-007-0014-8
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DOI: https://doi.org/10.1007/s12039-007-0014-8