Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin

Sengupta, Pradeep K.; Kasha, Michael

doi:10.1016/0009-2614(79)87221-8

Cited by 593 publications

(437 citation statements)

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“…This may be rationalized in terms of a greater hydrogen bonding of 2PBI with sucrose, whereby "blocked structure" might be formed analogous to the case of 3-hydroxyflavone. 32 Such blocked structures are known to hinder ESPT to a significant extent. Alternatively, the decrease in the dielectric constant of the solution might also play an important role here.…”

Section: Resultsmentioning

confidence: 99%

Early events associated with the excited state proton transfer in 2-(2′-pyridyl)benzimidazole

Burai

Mukherjee²,

Lahiri³

et al. 2009

The Journal of Chemical Physics

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2-͑2Ј-pyridyl͒benzimidazole ͑2PBI͒ undergoes excited state proton transfer ͑ESPT͒ in acidic solutions, leading to a tautomer emission at 460 nm. This photoprocess has been studied using ultrafast fluorescence spectroscopic techniques in acidic neat aqueous solutions, in viscous mixtures of glycerol with water, as well as in sucrose solutions. The tautomer is found to be stabilized in the more viscous medium, leading to a greater relative quantum yield as well as lifetime. The long rise time in tautomer emission is not affected by viscosity though. Rather, it appears to have the same value as the long component of the decay of the cationic excited state ͑C ‫ء‬ ͒. In addition to the subnanosecond lifetime reported earlier, C ‫ء‬ is found to exhibit a decay time of 2 ps. This is assigned to its protonation to form the nonfluorescent dication in its excited state ͑D ‫ء‬ ͒ considering the ground and excited state pK a values reported earlier. An additional rising component of 100 ps is observed in the region of C ‫ء‬ emission. This is likely to arise from a structural change or charge redistribution in C ‫ء‬ immediately after its creation and before the phototautomerization.

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Section: Resultsmentioning

confidence: 99%

Early events associated with the excited state proton transfer in 2-(2′-pyridyl)benzimidazole

Burai

Mukherjee²,

Lahiri³

et al. 2009

The Journal of Chemical Physics

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“…These molecules exhibit an excited-state intramolecular protontransfer (ESIPT) reaction and consequently a dual fluorescence with two emission bands, corresponding to the initially excited normal (N*) and reaction product tautomer (T*) forms (26). The introduction of charges in proximity but not in direct conjugation with the chromophore not only shifts the absorption and emission bands in accordance with electrochromic mechanisms but also changes dramatically the intensity ratio of the N* and T* band in accordance with the spectral shifts (25).…”

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confidence: 99%

Ultrasensitive two-color fluorescence probes for dipole potential in phospholipid membranes

Klymchenko

Duportail

Mély

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

138

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The principle of electrochromic modulation of excited-state intramolecular proton-transfer reaction was applied for the design of fluorescence probes with high two-color sensitivity to dipole potential, ⌿ d, in phospholipid bilayers. We report on the effect of ⌿ d variation on excitation and fluorescence spectra of two new 3-hydroxyflavone probes, which possess opposite orientations of the fluorescent moiety in the lipid bilayer. The dipole potential in the bilayer was modulated by the addition of 6-ketocholestanol or phloretin and by substitution of dimyristoyl phosphatidylcholine lipid with its ether analog 1,2-di-o-tetradecylsn-glycero-3-phosphocholine, and its value was estimated by the reference styryl dye 1-(3-sulfonatopropyl)-4-{␤[2-(di-noctylamino)-6-naphthyl]vinyl}pyridinium betaine. We demonstrate that after ⌿ d changes, the probe orienting in the bilayer similarly to the reference dye shows similar shifts in the excitation spectra, whereas the probe with the opposite orientation shows the opposite shifts. The new observation is that the response of 3-hydroxyflavone probes to ⌿ d in excitation spectra is accompanied by and quantitatively correlated with dramatic changes of relative intensities of the two well separated emission bands that belong to the initial normal and the product tautomer forms of the excited-state intramolecular proton-transfer reaction. This provides a strong response to ⌿ d by change in emission color.3-hydroxyflavone dyes ͉ two-color ratiometric probes

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“…The QCT with the 5-OH group has been known as a nonfluorescent compound in aqueous solutions. [10][11][12] However, it gave new fluorescence emission spectra in various hydroorganic mixed solvents when it was excited to the second excited state under 255 nm light, which corresponded to the maximum absorption of Band II. However, when 370 nm radiation, which corresponded to the maximum absorption of Band I, was used as the excitation source, no fluorescence emission was observed in the same mixed solvents.…”

Section: Resultsmentioning

confidence: 99%

“…[1][2][3][4][5][6] QCT is remarkable for its properties to mitigate the increase in capillary fragility, to reduce high blood pressure, to protect plants against the direct and indirect influences of UV radiation and to show antioxidant behaviors against a wide range of free radicals. [7][8][9][10][11][12] Flavonoids are well known compounds that exhibit characteristic fluorescence properties. 10,13 QCT has been considered to be composed of a special class of nonfluorescent molecules.…”

Section: Introductionmentioning

confidence: 99%

“…10,13 QCT has been considered to be composed of a special class of nonfluorescent molecules. [10][11][12] However, a new significant fluorescence emission was discovered in CH 3 OH-H 2 O and CH 3 CN-H 2 O mixed solvents. 14 It would be, therefore, very interesting to study the physicochemical properties of QCT in a specific environment, especially in vivo, to better understand the mechanism of its strong biological activity.…”

Section: Introductionmentioning

confidence: 99%

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Spectroscopic Properties of Quercetin in AOT Reverse Micelles

Park¹,

Im²,

Seo³

et al. 2014

Bulletin of the Korean Chemical Society

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The spectroscopic properties of quercetin (QCT) were studied in the AOT reverse micelle by fluorescence spectroscopy. Because the molecular structure of QCT is completely planar, excited state intramolecular proton transfer (ESIPT) occurs between the -OH at C(5) and carbonyl oxygen via intramolecular hydrogen bonding. This ESIPT happens at the S1 state but not at the S2 state. Because QCT is a good donor-acceptor-conjugated molecule at the excited state, this molecule can emit strong fluorescence but shows no S1 → So emission due to this ESIPT. Since the S2 → S1 internal conversion was very slow due to the small Franck-Condon factors, S2 → So fluorescence emission was observed. All of the experimental results indicated that the QCT resided at the bound water interface and that the position of solute did not change significantly in the micelle at various water concentrations.

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Excited state proton-transfer spectroscopy of 3-hydroxyflavone and quercetin

Cited by 593 publications

References 4 publications

Early events associated with the excited state proton transfer in 2-(2′-pyridyl)benzimidazole

Early events associated with the excited state proton transfer in 2-(2′-pyridyl)benzimidazole

Ultrasensitive two-color fluorescence probes for dipole potential in phospholipid membranes

Spectroscopic Properties of Quercetin in AOT Reverse Micelles

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