메뉴 건너뛰기




Volumn 5, Issue 11, 2006, Pages 1038-1044

Modulation of dual fluorescence in a 3-hydroxyquinolone dye by perturbation of its intramolecular proton transfer with solvent polarity and basicity

Author keywords

[No Author keywords available]

Indexed keywords

1 METHYL 2 (4 METHOXY)PHENYL 3 HYDROXY 4(1H) QUINOLONE; 3 HYDROXYQUINOLONE; ACETIC ACID ETHYL ESTER; ACETONITRILE; DYE; N,N DIMETHYLFORMAMIDE; QUINOLONE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 33750555117     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b610054f     Document Type: Article
Times cited : (42)

References (57)
  • 2
    • 33846450875 scopus 로고    scopus 로고
    • Ratio imaging: Practical considerations for measuring intracellular calcium and pH in living tissue
    • R. B. Silver Ratio imaging: practical considerations for measuring intracellular calcium and pH in living tissue Methods Cell Biol. 1998 56 237.
    • (1998) Methods Cell Biol. , vol.56 , pp. 237
    • Silver, R.B.1
  • 3
    • 0142231517 scopus 로고    scopus 로고
    • Structural changes accompanying intramolecular electron transfer: Focus on twisted intramolecular charge-transfer states and structures
    • Z. R. Grabowski K. Rotkiewicz W. Rettig Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures Chem. Rev. 2003 103 3899.
    • (2003) Chem. Rev. , vol.103 , pp. 3899
    • Grabowski, Z.R.1    Rotkiewicz, K.2    Rettig, W.3
  • 4
    • 0004382723 scopus 로고
    • Excited-state proton transfer reactions II. Intramolecular, reactions
    • S. J. Formosinho L. G. Arnaut Excited-state proton transfer reactions II. Intramolecular, reactions J. Photochem. Photobiol., A 1993 75 21.
    • (1993) J. Photochem. Photobiol., A , vol.75 , pp. 21
    • Formosinho, S.J.1    Arnaut, L.G.2
  • 5
    • 0000734502 scopus 로고
    • Excited state intramolecular proton transfer. Part 2. ESIPT to oxygen
    • D. Le Gourrierec S. M. Ormson R. G. Brown Excited state intramolecular proton transfer. Part 2. ESIPT to oxygen Prog. React. Kinet. 1994 19 211.
    • (1994) Prog. React. Kinet. , vol.19 , pp. 211
    • Le Gourrierec, D.1    Ormson, S.M.2    Brown, R.G.3
  • 7
    • 0037198802 scopus 로고    scopus 로고
    • Excited state intramolecular proton transfer and metal ion complexation of 2-(2′-hydroxyphenyl)benzazoles in aqueous solution
    • M. Henary C. Fahrni Excited state intramolecular proton transfer and metal ion complexation of 2-(2′-hydroxyphenyl)benzazoles in aqueous solution J. Phys. Chem. A 2002 106 5210.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 5210
    • Henary, M.1    Fahrni, C.2
  • 8
    • 0032560468 scopus 로고    scopus 로고
    • A coupled proton-transfer and twisting-motion fluorescence probe for lipid bilayers
    • C. R. Mateo A. Douhal A coupled proton-transfer and twisting-motion fluorescence probe for lipid bilayers Proc. Natl. Acad. Sci. U. S. A. 1998 95 7245.
    • (1998) Proc. Natl. Acad. Sci. U. S. A. , vol.95 , pp. 7245
    • Mateo, C.R.1    Douhal, A.2
  • 9
    • 0002521341 scopus 로고    scopus 로고
    • Excited state intramolecular proton transfer in 2-(2′-benzamidophenyl) benzimidazole: Effect of solvents
    • S. Santra G. Krishnamoorthy S. K. Dogra Excited state intramolecular proton transfer in 2-(2′-benzamidophenyl) benzimidazole: effect of solvents Chem. Phys. Lett. 1999 311 55.
    • (1999) Chem. Phys. Lett. , vol.311 , pp. 55
    • Santra, S.1    Krishnamoorthy, G.2    Dogra, S.K.3
  • 10
    • 0242594152 scopus 로고    scopus 로고
    • Excited-state intramolecular proton transfer (ESIPT) in 2-(2′-hydroxyphenyl)-oxazole and -thiazole
    • D. Le Gourrierec V. A. Kharlanov R. G. Brown W. Rettig Excited-state intramolecular proton transfer (ESIPT) in 2-(2′-hydroxyphenyl)-oxazole and -thiazole J. Photochem. Photobiol., A 2000 130 101.
    • (2000) J. Photochem. Photobiol., A , vol.130 , pp. 101
    • Le Gourrierec, D.1    Kharlanov, V.A.2    Brown, R.G.3    Rettig, W.4
  • 11
    • 0000579491 scopus 로고
    • Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin
    • P. K. Sengupta M. Kasha Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin Chem. Phys. Lett. 1979 68 382.
    • (1979) Chem. Phys. Lett. , vol.68 , pp. 382
    • Sengupta, P.K.1    Kasha, M.2
  • 12
    • 0004194845 scopus 로고
    • Proton-transfer spectroscopy of 3-hydroxyflavone in an isolated-site crystal matrix
    • D. McMorrow M. Kasha Proton-transfer spectroscopy of 3-hydroxyflavone in an isolated-site crystal matrix J. Phys. Chem. 1984 88 2235.
    • (1984) J. Phys. Chem. , vol.88 , pp. 2235
    • McMorrow, D.1    Kasha, M.2
  • 13
    • 0000672351 scopus 로고
    • Proton transfer dynamics in substituted 3-hydroxyflavones: Solvent polarization effects
    • T. C. Swiney F. D. Kelley Proton transfer dynamics in substituted 3-hydroxyflavones: Solvent polarization effects J. Chem. Phys. 1993 99 211.
    • (1993) J. Chem. Phys. , vol.99 , pp. 211
    • Swiney, T.C.1    Kelley, F.D.2
  • 14
    • 0000654754 scopus 로고
    • Reversal of excitation behavior of proton-transfer vs. Charge-transfer by dielectric perturbation of electronic manifolds
    • P.-T. Chou M. L. Martinez J. H. Clements Reversal of excitation behavior of proton-transfer vs. charge-transfer by dielectric perturbation of electronic manifolds J. Phys. Chem. 1993 97 2618.
    • (1993) J. Phys. Chem. , vol.97 , pp. 2618
    • Chou, P.-T.1    Martinez, M.L.2    Clements, J.H.3
  • 15
    • 0002646635 scopus 로고
    • Switching between charge- and proton-transfer emission in the excited state of a substituted 3-hydroxyflavone
    • M. S. Ormson R. Brown G. F. Vollmer W. Rettig Switching between charge- and proton-transfer emission in the excited state of a substituted 3-hydroxyflavone J. Photochem. Photobiol. 1994 81 65.
    • (1994) J. Photochem. Photobiol. , vol.81 , pp. 65
    • Ormson, M.S.1    Brown, R.2    Vollmer, G.F.3    Rettig, W.4
  • 16
    • 0034886731 scopus 로고    scopus 로고
    • Synthesis and spectroscopic properties of benzo- and naphthofuryl-3-hydroxychromones
    • A. S. Klymchenko T. Oztürk V. G. Pivovarenko A. P. Demchenko Synthesis and spectroscopic properties of benzo- and naphthofuryl-3-hydroxychromones Can. J. Chem. 2001 79 358.
    • (2001) Can. J. Chem. , vol.79 , pp. 358
    • Klymchenko, A.S.1    Oztürk, T.2    Pivovarenko, V.G.3    Demchenko, A.P.4
  • 17
    • 0142125377 scopus 로고    scopus 로고
    • Modulation of the solvent-dependent dual emission in 3-hydroxychromones by substituents
    • A. S. Klymchenko V. G. Pivovarenko T. Oztürk A. P. Demchenko Modulation of the solvent-dependent dual emission in 3-hydroxychromones by substituents New J. Chem. 2003 27 1336.
    • (2003) New J. Chem. , vol.27 , pp. 1336
    • Klymchenko, A.S.1    Pivovarenko, V.G.2    Oztürk, T.3    Demchenko, A.P.4
  • 18
    • 0037163322 scopus 로고    scopus 로고
    • Synthesis of furanochromones: A new step in improvement of fluorescence properties
    • A. S. Klymchenko T. Oztürk A. P. Demchenko Synthesis of furanochromones: a new step in improvement of fluorescence properties Tetrahedron Lett. 2002 43 7079.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7079
    • Klymchenko, A.S.1    Oztürk, T.2    Demchenko, A.P.3
  • 20
    • 0037031232 scopus 로고    scopus 로고
    • Ultrasensitive fluorescent probe for the hydrophobic range of solvent polarities
    • S. Ercelen A. S. Klymchenko A. P. Demchenko Ultrasensitive fluorescent probe for the hydrophobic range of solvent polarities Anal. Chim. Acta 2002 464 273.
    • (2002) Anal. Chim. Acta , vol.464 , pp. 273
    • Ercelen, S.1    Klymchenko, A.S.2    Demchenko, A.P.3
  • 21
    • 0037526227 scopus 로고    scopus 로고
    • Elimination of the hydrogen bonding effect on the solvatochromism of 3-hydroxyflavones
    • A. S. Klymchenko V. G. Pivovarenko A. P. Demchenko Elimination of the hydrogen bonding effect on the solvatochromism of 3-hydroxyflavones J. Phys. Chem. A 2003 107 4211.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 4211
    • Klymchenko, A.S.1    Pivovarenko, V.G.2    Demchenko, A.P.3
  • 22
    • 0037208160 scopus 로고    scopus 로고
    • Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer
    • A. S. Klymchenko A. P. Demchenko Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer Phys. Chem. Chem. Phys. 2003 5 461.
    • (2003) Phys. Chem. Chem. Phys. , vol.5 , pp. 461
    • Klymchenko, A.S.1    Demchenko, A.P.2
  • 23
    • 0037120911 scopus 로고    scopus 로고
    • Electrochromic modulation of excited-state intramolecular proton transfer: The new principle in design of fluorescence sensors
    • A. S. Klymchenko A. P. Demchenko Electrochromic modulation of excited-state intramolecular proton transfer: The new principle in design of fluorescence sensors J. Am. Chem. Soc. 2002 124 12372.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12372
    • Klymchenko, A.S.1    Demchenko, A.P.2
  • 24
    • 0039270230 scopus 로고    scopus 로고
    • Effect of reverse micelles on the intramolecular excited state proton transfer (ESPT) and dual luminescence behaviour of 3-hydroxyflavone
    • M. Sarkar J. G. Ray P. K. Sengupta Effect of reverse micelles on the intramolecular excited state proton transfer (ESPT) and dual luminescence behaviour of 3-hydroxyflavone Spectrochim. Acta, Part A 1996 52 275.
    • (1996) Spectrochim. Acta , vol.52 , pp. 275
    • Sarkar, M.1    Ray, J.G.2    Sengupta, P.K.3
  • 25
    • 0028481269 scopus 로고
    • Synthesis and characterization of wavelength-shifting monomers and polymers based on 3-hydroxyflavone
    • J. R. Dharia K. F. Johnson J. B. Schlenoff Synthesis and characterization of wavelength-shifting monomers and polymers based on 3-hydroxyflavone Macromolecules 1994 27 5167.
    • (1994) Macromolecules , vol.27 , pp. 5167
    • Dharia, J.R.1    Johnson, K.F.2    Schlenoff, J.B.3
  • 26
    • 0037162573 scopus 로고    scopus 로고
    • Probing AOT reverse micelles with two-color fluorescence dyes based on 3-hydroxychromone
    • A. S. Klymchenko A. P. Demchenko Probing AOT reverse micelles with two-color fluorescence dyes based on 3-hydroxychromone Langmuir 2002 18 5637.
    • (2002) Langmuir , vol.18 , pp. 5637
    • Klymchenko, A.S.1    Demchenko, A.P.2
  • 27
    • 0036849912 scopus 로고    scopus 로고
    • Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes
    • A. S. Klymchenko G. Duportail T. Oztürk V. G. Pivovarenko Y. Mély A. P. Demchenko Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes Chem. Biol. 2002 9 1199.
    • (2002) Chem. Biol. , vol.9 , pp. 1199
    • Klymchenko, A.S.1    Duportail, G.2    Oztürk, T.3    Pivovarenko, V.G.4    Mély, Y.5    Demchenko, A.P.6
  • 29
    • 0028032854 scopus 로고
    • Interplay between excited-state intramolecular proton transfer and charge transfer in flavonols and their use as protein-binding-site fluorescence probes
    • A. Sytnik D. Gormin M. Kasha Interplay between excited-state intramolecular proton transfer and charge transfer in flavonols and their use as protein-binding-site fluorescence probes Proc. Natl. Acad. Sci. U. S. A. 1994 91 11968.
    • (1994) Proc. Natl. Acad. Sci. U. S. A. , vol.91 , pp. 11968
    • Sytnik, A.1    Gormin, D.2    Kasha, M.3
  • 30
    • 0032472822 scopus 로고    scopus 로고
    • Flavonols-new fluorescent membrane probes for studying the interdigitation of lipid bilayers
    • O. P. Bondar V. G. Pivovarenko E. S. Rowe Flavonols-new fluorescent membrane probes for studying the interdigitation of lipid bilayers Biochim. Biophys. Acta 1998 1369 119.
    • (1998) Biochim. Biophys. Acta , vol.1369 , pp. 119
    • Bondar, O.P.1    Pivovarenko, V.G.2    Rowe, E.S.3
  • 32
    • 0037434886 scopus 로고    scopus 로고
    • Novel two-color fluorescence probe with extreme specificity to bovine serum albumin
    • S. Ercelen A. S. Klymchenko A. P. Demchenko Novel two-color fluorescence probe with extreme specificity to bovine serum albumin FEBS Lett. 2003 538 25.
    • (2003) FEBS Lett. , vol.538 , pp. 25
    • Ercelen, S.1    Klymchenko, A.S.2    Demchenko, A.P.3
  • 33
    • 2342469959 scopus 로고    scopus 로고
    • Application of two-color ratiometric site-selective fluorescence probes and labels in protein research
    • A. S. Klymchenko S. V. Avilov A. P. Demchenko Application of two-color ratiometric site-selective fluorescence probes and labels in protein research Anal. Biochem. 2004 329 43.
    • (2004) Anal. Biochem. , vol.329 , pp. 43
    • Klymchenko, A.S.1    Avilov, S.V.2    Demchenko, A.P.3
  • 35
    • 1342265021 scopus 로고    scopus 로고
    • The photophysics of some 3-hydroxyflavone derivatives in the presence of protons, alkali metal and alkaline earth cations
    • X. Poteau G. Saroja C. Spies R. G. Brown The photophysics of some 3-hydroxyflavone derivatives in the presence of protons, alkali metal and alkaline earth cations J. Phys. Chem. A 2004 162 431.
    • (2004) J. Phys. Chem. A , vol.162 , pp. 431
    • Poteau, X.1    Saroja, G.2    Spies, C.3    Brown, R.G.4
  • 36
    • 33645682613 scopus 로고    scopus 로고
    • Fluorometric detection of adenosine triphosphate with 3-hydroxy-4′-(Dimethylamino)flavone in aqueous solutions
    • V. G. Pivovarenko O. B. Vadzyuk S. O. Kosterin Fluorometric detection of adenosine triphosphate with 3-hydroxy-4′-(dimethylamino)flavone in aqueous solutions J. Fluoresc. 2006 16 9.
    • (2006) J. Fluoresc. , vol.16 , pp. 9
    • Pivovarenko, V.G.1    Vadzyuk, O.B.2    Kosterin, S.O.3
  • 37
    • 0000647729 scopus 로고    scopus 로고
    • Ring closing and photooxidation in nitrogen analogues of 3-hydroxyflavone
    • F. Gao K. F. Johnson J. B. Schlenoff Ring closing and photooxidation in nitrogen analogues of 3-hydroxyflavone J. Chem. Soc., Perkin Trans. 2 1996 2 269.
    • (1996) J. Chem. Soc., Perkin Trans. 2 , vol.2 , pp. 269
    • Gao, F.1    Johnson, K.F.2    Schlenoff, J.B.3
  • 39
    • 33646594106 scopus 로고    scopus 로고
    • 2-Aryl-3-hydroxyquinolones, a new class of dyes with solvent dependent dual emission due to excited state intramolecular proton transfer
    • D. A. Yushchenko V. V. Shvadchak A. S. Klymchenko G. Duportail Y. Mély V. G. Pivovarenko 2-Aryl-3-hydroxyquinolones, a new class of dyes with solvent dependent dual emission due to excited state intramolecular proton transfer New J. Chem. 2006 30 774.
    • (2006) New J. Chem. , vol.30 , pp. 774
    • Yushchenko, D.A.1    Shvadchak, V.V.2    Klymchenko, A.S.3    Duportail, G.4    Mély, Y.5    Pivovarenko, V.G.6
  • 40
    • 10744233382 scopus 로고    scopus 로고
    • Picosecond time-resolved fluorescence studies are consistent with reversible excited-state intramolecular proton transfer in 4′-(Dialkylaminoe)-3-hydroxyflavones
    • V. V. Shynkar Y. Mély G. Duportail E. Piémont A. S. Klymchenko A. P. Demchenko Picosecond time-resolved fluorescence studies are consistent with reversible excited-state intramolecular proton transfer in 4′-(dialkylaminoe)-3-hydroxyflavones J. Phys. Chem. A 2003 107 9522.
    • (2003) J. Phys. Chem. A , vol.107 , pp. 9522
    • Shynkar, V.V.1    Mély, Y.2    Duportail, G.3    Piémont, E.4    Klymchenko, A.S.5    Demchenko, A.P.6
  • 41
    • 0141849929 scopus 로고    scopus 로고
    • Tuning the mechanism of proton-transfer in a hydroxyflavone derivative
    • A. D. Roshal J. A. Organero A. Douhal Tuning the mechanism of proton-transfer in a hydroxyflavone derivative Chem. Phys. Lett. 2003 379 53.
    • (2003) Chem. Phys. Lett. , vol.379 , pp. 53
    • Roshal, A.D.1    Organero, J.A.2    Douhal, A.3
  • 42
    • 36849108026 scopus 로고
    • Band shapes of the electronic spectra of complex molecules
    • D. B. Siano D. E. Metzler Band shapes of the electronic spectra of complex molecules J. Chem. Phys. 1969 51 1856.
    • (1969) J. Chem. Phys. , vol.51 , pp. 1856
    • Siano, D.B.1    Metzler, D.E.2
  • 44
    • 0001464493 scopus 로고
    • Analyzing the distribution of decay constants in pulse-fluorimetry using the maximum entropy method
    • A. K. Livesey J.-C. Brochon Analyzing the distribution of decay constants in pulse-fluorimetry using the maximum entropy method Biophys. J. 1987 52 693.
    • (1987) Biophys. J. , vol.52 , pp. 693
    • Livesey, A.K.1    Brochon, J.-C.2
  • 46
    • 0041573625 scopus 로고
    • Linear salvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation
    • M. J. Kamlet J. L. M. Abboud M. H. Abraham R. W. Taft Linear salvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation J. Org. Chem. 1983 48 2877.
    • (1983) J. Org. Chem. , vol.48 , pp. 2877
    • Kamlet, M.J.1    Abboud, J.L.M.2    Abraham, M.H.3    Taft, R.W.4
  • 47
    • 0027982335 scopus 로고
    • Hydrogen bonding. 32. An analysis of water–octanol and water–alkane partitioning and the delta log P parameter of seiler
    • M. H. Abraham H. S. Chadha G. S. Whiting R. C. Mitchell Hydrogen bonding. 32. An analysis of water–octanol and water–alkane partitioning and the delta log P parameter of seiler J. Pharm. Sci. 1994 83 1085.
    • (1994) J. Pharm. Sci. , vol.83 , pp. 1085
    • Abraham, M.H.1    Chadha, H.S.2    Whiting, G.S.3    Mitchell, R.C.4
  • 48
    • 0036837584 scopus 로고    scopus 로고
    • Dipole moments of 4′-aminoflavonols determined using electro-optical absorption measurements or molecular Stark-effect spectroscopy
    • N. A. Nemkovich W. Baumann V. G. Pivovarenko Dipole moments of 4′-aminoflavonols determined using electro-optical absorption measurements or molecular Stark-effect spectroscopy J. Photochem. Photobiol., A 2002 153 19.
    • (2002) J. Photochem. Photobiol., A , vol.153 , pp. 19
    • Nemkovich, N.A.1    Baumann, W.2    Pivovarenko, V.G.3
  • 49
    • 0343791148 scopus 로고
    • Electric moments of molecules in liquids
    • L. J. Onsager Electric moments of molecules in liquids Am. Chem. Soc. 1936 58 1486.
    • (1936) Am. Chem. Soc. , vol.58 , pp. 1486
    • Onsager, L.J.1
  • 51
    • 0003907064 scopus 로고
    • Academic Press, New York
    • W. Liptay, in Excited States, Academic Press, New York, 1974, p. 129.
    • (1974) Excited States , pp. 129
    • Liptay, W.1
  • 55
    • 33845560314 scopus 로고
    • Analysis of two-state excited-state reactions. The fluorescence decay of 2-naphthol
    • W. R. Laws L. Brand Analysis of two-state excited-state reactions. The fluorescence decay of 2-naphthol J. Phys. Chem. 1979 83 795.
    • (1979) J. Phys. Chem. , vol.83 , pp. 795
    • Laws, W.R.1    Brand, L.2
  • 56
  • 57
    • 0142044626 scopus 로고    scopus 로고
    • Perturbation of planarity as the possible mechanism of solvent-dependent variations of fluorescence quantum yield in 2-aryl-3-hydroxychromones
    • A. S. Klymchenko V. G. Pivovarenko A. P. Demchenko Perturbation of planarity as the possible mechanism of solvent-dependent variations of fluorescence quantum yield in 2-aryl-3-hydroxychromones Spectrochim. Acta, Part A 2003 59 787.
    • (2003) Spectrochim. Acta, Part A , vol.59 , pp. 787
    • Klymchenko, A.S.1    Pivovarenko, V.G.2    Demchenko, A.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.