Site selectivity in excited-state intramolecular proton transfer in flavonols

Nemkovich, N. A.; Kruchenok, Julia V.; Рубинов, А. Н.; Pivovarenko, Vasyl G.; Baumann, Wolfram

doi:10.1016/s1010-6030(00)00408-1

Cited by 51 publications

(24 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The red-edge effects for ESPT in different 3-hydroxyflavone derivatives were studied in different heterogenic and motionally restricted environmentsmicelles and lipid bilayers (96)(97)(98)(99), protein molecules (25, 100), phospholipid bilayers (101) and cell membranes (102). In all cases, photoselection at the red-edge suppressed the PT reaction.…”

Section: Excited-state Proton Transfermentioning

confidence: 99%

The red‐edge effects: 30 years of exploration

2002

View full text Add to dashboard Cite

In 1970, three laboratories independently made a discovery that, for aromatic fluorophores embedded into different rigid and highly viscous media, the spectroscopic properties do not conform to classical rules. The fluorescence spectra can depend on excitation wavelength, and the excited-state energy transfer, if present, fails at the "red" excitation edge. These red-edge effects were related to the existence of excited-state distribution of fluorophores on their interaction energy with the environment and the slow rate of dielectric relaxation of this environment. In these conditions the site-selection can be provided by variation of the energy of illuminating light quanta, and the behaviour of selected species can be followed as a function of time and other variables. These observations found extensive application in different areas of research: colloid and polymer science, molecular biophysics, photochemistry and photobiology. In particular, they led to the development of very productive methods of studying the dynamics of dielectric relaxations in protein and membranes, using the tryptophan emission and the emission of a variety of probes. These studies were extended to the time domain with the observation of new site-selective effects in emission intensity and anisotropy decays. They stimulated the emergence and development of cryogenic energy-selective and single-molecular techniques that became valuable tools in their own right in chemistry and biophysics research. Site-selection effects were discovered for electron-transfer and proton-transfer reactions if they depended on the dynamics of the environment. This review is focused on the progress in the field of red-edge effects, their applications and prospects.

show abstract

Section: Excited-state Proton Transfermentioning

confidence: 99%

The red‐edge effects: 30 years of exploration

2002

View full text Add to dashboard Cite

show abstract

“…The range of the inhomogeneous broadening, which dictates photoselection of the energetically different species, depends on the values of dipole moments of the dye molecules in the ground and excited states, and on the dielectric properties and structure of a solvent [11, 12]. …”

Section: Theoretical Backgroundmentioning

confidence: 99%

“…Recently, several theoretical models of the solvation of molecule in liquid solvent have been developed [ 1 ]. Phenomenological description of inhomogeneous broadening of electronic spectra of organic molecules in solution has been given by Nemkovich et al [ 11 , 12 ]. They proposed a free energy diagram which describes the dependence of the free energy of the probe-environment centers (solvates) on the strength of the local electric field.…”

Section: Theoretical Backgroundmentioning

confidence: 99%

Excitation-wavelength Dependent Fluorescence of Ethyl 5-(4-aminophenyl)-3-amino-2,4-dicyanobenzoate

Józefowicz

Heldt

2010

J Fluoresc

View full text Add to dashboard Cite

The excitation wavelength dependence of the steady-state and time-resolved emission spectra of ethyl 5-(4-aminophenyl)-3-amino-2,4-dicyanobenzoate (EAADCy) in tetrahydrofuran (THF) at room temperature has been examined. It is found that the ratio of the fluorescence intensity of the long-wavelength and short-wavelength fluorescence bands strongly depends on the excitation wavelength, whereas the wavelengths of the fluorescence excitation and fluorescence bands maxima are independent on the observation/excitation wavelengths. The dynamic Stokes shift of fluorophore in locally excited (LE) and intramolecular charge transfer (ICT) states has been studied with a time resolution about 30 ps. The difference between Stokes shift in the LE and ICT states was attributed to the solvent response to the large photoinduced dipole moment of EAADCy in the fluorescent charge transfer state. On this base we can state that, the relaxation of the polar solvent molecules around the fluorophore was observed.

show abstract

“…This was shown for local fields, generated by the surrounding molecules [7][8][9][10][11][12][13][14][15][16][17][18][19][20] or for dipole potential of lipid membrane [21], as well as for general ones, caused by charged poles of electro-optical cell [22][23][24]. The mentioned results point to good aspects of the utilization of 3-hydroxyflavones in the design of probe for tetra-charged ATP anion determination.…”

Section: Introductionmentioning

confidence: 96%

Fluorometric Detection of Adenosine Triphosphate with 3-Hydroxy-4′-(dimethylamino)flavone in Aqueous Solutions

2006

View full text Add to dashboard Cite

An effect of appearance of new band in the excitation spectra of 3-hydroxy-4 -(dimethylamino)flavone (FME probe) in presence of adenosine triphosphate (ATP) is described. Considerable shift of new band up to the red and increase of fluorescence intensity points to the formation of FME-ATP associate, in which FME molecule undergoes to a strong electrostatic stabilization by tetra-charged ATP anion. It is shown the FME anion formation is possible under influence of ATP in the studied conditions. The dynamics of the observed effect is studied in mitochondria. The registered phenomenon allows the quantitative evaluation of ATP concentration in the range of 10 −3 -10 −5 M. In contrast to ATP, other nucleoside phosphates do not give a new band in the excitation spectra of FME probe. This implies the possibility of the in vivo determination of the ATP concentration.

show abstract

Site selectivity in excited-state intramolecular proton transfer in flavonols

Cited by 51 publications

References 50 publications

The red‐edge effects: 30 years of exploration

The red‐edge effects: 30 years of exploration

Excitation-wavelength Dependent Fluorescence of Ethyl 5-(4-aminophenyl)-3-amino-2,4-dicyanobenzoate

Fluorometric Detection of Adenosine Triphosphate with 3-Hydroxy-4′-(dimethylamino)flavone in Aqueous Solutions

Contact Info

Product

Resources

About