Spectroscopic properties of ethyl 5-(4-aminophenyl)-3-amino-2,4-dicyanobenzoate

Józefowicz, Marek; Aleksiejew, Marek; Bajorek, Agnieszka; Pączkowski, Jerzy; Heldt, J.

doi:10.1016/j.chemphys.2007.07.035

Cited by 22 publications

(17 citation statements)

References 25 publications

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“…We characterized this specific behavior for ethyl 5-(4-aminophenyl)-3-amino-2,4-dicyanobenzoate in our earlier papers [18,19]. Described in this communication ethyl 5-(4-dimethylaminophenyl)-3-amino-2,4-dicyanobenzoate shows similar properties.…”

Section: Angle D (°)mentioning

confidence: 70%

“…The range of the inhomogeneous broadening, Dm inh , which dictates photoselection of the energetically different species, depends on the values of dipole moments of the dye molecule in the ground and excited states, and on the dielectric properties and structure of a solvent. It has been shown in our previous papers [5,18,19], that for laurdan dissolved in AcN the estimated value of Dm inh at room temperature is about 700 cm À1 and for EAADCy dissolved in THF is about 900 and 100 cm À1 for planar and perpendicular form, respectively.…”

Section: Determination Of Reorganization Energy Of Edmaadcy In Neat Smentioning

confidence: 96%

“…Described in our earlier papers ethyl 5-(4-aminophenyl)-3-amino-2,4-dicyanobenzoate (EAADCy) [18,19] is the example of such probe. Studies in different solvents, as well as semiempirical calculations performed for this molecule, indicate that conformations with donor and acceptor groups coplanar absorb and emit at wavelengths that are longer than those observed for donor-acceptor groups oriented orthogonally.…”

Section: Introductionmentioning

confidence: 99%

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Spectroscopic properties of ethyl 5-(4-dimethylaminophenyl)-3-amino-2,4-dicyanobenzoate

Józefowicz¹,

Heldt²,

Bajorek³

et al. 2009

Chemical Physics

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Dedicated to Professor Józef Heldt on the occasion of his 75th birthday Keywords:Ethyl 5-(4-dimethylaminophenyl)-3-amino-2,4-dicyanobenzoate Charge transfer fluorescence Donor-acceptor system a b s t r a c tWe report the synthesis and photophysical properties of ethyl 5-(4-dimethylaminophenyl)-3-amino-2,4-dicyanobenzoate (EDMAADCy) in neat solvents of different polarity. The relation between molecular conformations of molecule under study and spectral behavior has been studied using steady-state spectroscopic technique, electrochemical measurements, and quantum-chemical calculations. The fluorescence spectra of EDMAADCy possess, in medium polar solvents, two bands. Theoretical studies of the TICT phenomenon have been made in order to explain the dual emission of the molecule under study. Calculated electric dipole moments in the ground and excited states, for perpendicular and flatted conformers, have been compared with experimentally determined data. Additionally, the results of spectroscopic measurements were used to calculate, according to Marcus theory, the outer-sphere solvent reorganization energy and the internal molecular reorganization energy.

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Section: Angle D (°)mentioning

confidence: 70%

Section: Determination Of Reorganization Energy Of Edmaadcy In Neat Smentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Spectroscopic properties of ethyl 5-(4-dimethylaminophenyl)-3-amino-2,4-dicyanobenzoate

Józefowicz¹,

Heldt²,

Bajorek³

et al. 2009

Chemical Physics

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“…We found that for EAADCy molecule the ground-state rotational potential is essentially flat (in the range from 60° to 120°) [18, 19]. Figure 1a shows the calculated ground-state ( S 0 ) rotational potential and the corresponding rotamer distribution function n ( φ ) determined from Boltzmann’s low at 298 K, for the molecule under study.…”

Section: Resultsmentioning

confidence: 99%

“…To test whether the changes in the absorption, fluorescence excitation and fluorescence spectra originate from the solute conformers possesing different angles between their interatomic planes of the donor and acceptor moieties, a series of conformational semiempirical quantum mechanical calculations were carried out. We found that for EAADCy molecule the ground-state rotational potential is essentially flat (in the range from 60° to 120°) [ 18 , 19 ]. Figure 1a shows the calculated ground-state ( S 0 ) rotational potential and the corresponding rotamer distribution function n ( φ ) determined from Boltzmann’s low at 298 K, for the molecule under study.…”

Section: Resultsmentioning

confidence: 99%

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

Józefowicz

Heldt

2010

J Fluoresc

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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.

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New highly fluorescent hybrids (benz)imidazol-2-aminonicotinonitrile and -2-aminoisophthalonitrile: synthesis, characterization, fluorescence study, and theoretical calculations

Boulebd¹,

Ismaïli²,

Khatyr³

et al. 2018

Monatsh Chem

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Spectroscopic properties of ethyl 5-(4-aminophenyl)-3-amino-2,4-dicyanobenzoate

Cited by 22 publications

References 25 publications

Spectroscopic properties of ethyl 5-(4-dimethylaminophenyl)-3-amino-2,4-dicyanobenzoate

Spectroscopic properties of ethyl 5-(4-dimethylaminophenyl)-3-amino-2,4-dicyanobenzoate

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

New highly fluorescent hybrids (benz)imidazol-2-aminonicotinonitrile and -2-aminoisophthalonitrile: synthesis, characterization, fluorescence study, and theoretical calculations

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