Effect of hydrogen bonding on the intramolecular charge transfer fluorescence of 6-dodecanoyl-2-dimethylaminonaphtalene

Józefowicz, Marek; Kozyra, K. A.; Heldt, J.

doi:10.1016/j.chemphys.2005.06.021

Cited by 48 publications

(34 citation statements)

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“…Fluorescent probes such as prodan (6-propionyl-2-dimethylaminonaphthalene) and laurdan (6-dodecanoyl-2-dimethylaminonaphthalene) are widely used in biological and biophysical research [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. The fluorescence properties of prodan and laurdan have been described in the literature as simultaneously existing local-excited (LE) and twisted internal charge-transfer (TICT) states.…”

Section: 37mentioning

confidence: 99%

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Effect of proton-donor solvent and structural flexibility of prodan and laurdan molecules on their spectral-luminescent properties

et al. 2009

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535.37The influence of structural flexibility on dipole moments, energy-level locations, and charge distributions in prodan and laurdan molecules was studied. A quantum-chemical calculation of isolated prodan and laurdan molecules in the fluorescent state geometry was conducted. Rate constants for radiative and non-radiative processes and fluorescence quantum yields for these probe molecules were calculated. Interaction centers of prodan and laurdan with a proton-donor solvent were estimated quantitatively. The possibility of using fluorescent probes for estimating the polarity of proton-donor and proton-acceptor solvents was shown.Keywords: fluorescent probe, prodan, laurdan, structural flexibility, proton-donor properties, fluorescence quantum yield.Introduction. Fluorescent probes such as prodan (6-propionyl-2-dimethylaminonaphthalene) and laurdan (6-dodecanoyl-2-dimethylaminonaphthalene) are widely used in biological and biophysical research [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. The fluorescence properties of prodan and laurdan have been described in the literature as simultaneously existing local-excited (LE) and twisted internal charge-transfer (TICT) states. However, the latter term should be used very arbitrarily because the state has been observed only at very low temperatures [2]. These states are strongly delocalized at temperatures near ambient and above [2]. It has been shown [5] that the positions of fluorescence maxima in phospholipids bilayers depend on the phase state of the phospholipids, i.e., 435 and 440 nm for the short-wavelength band in the gel phase; 515 and 490 nm, for prodan and laurdan in the liquid-crystalline phase. Two fluorescence bands (430 and 500 nm) were observed for laurdan in glycerin with λ ex = 380 nm at room temperature. The short-wavelength band at 430 nm disappeared as the temperature was raised to 370 K.The large shifts of prodan and laurdan fluorescence bands in solvents of different polarity have been explained by the significant change of dipole moment in the excited state as compared with the ground state. According to formulas for calculating common effects of solvents [16,17], changing the prodan dipole moment from 5.5 to 10.2 D causes a shift of the S 0 → S 1 -transition [18,19] in its fluorescence spectra of 770 cm -1 and 800 cm -1 on going to isopropanol and water, respectively, from a non-polar solvent [19,20]. The experimental shifts in fluorescence spectra of prodan were 3790 and 5520 cm -1 in isopropanol and water, i.e., the size of the dipole moment and its change from

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Section: 37mentioning

confidence: 99%

“…The effect of H-bonds on the shift of absorption and fluorescence bands of laurdan in a methylcyclohexaneethanol mixture has been studied [7]. It was shown that the shift was due to formation of a 1:1 complex of laurdan Fig.…”

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Effect of proton-donor solvent and structural flexibility of prodan and laurdan molecules on their spectral-luminescent properties

et al. 2009

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“…In general, for the probing of the changes in properties of environment many various probes' ''responses" can be used. These include: the changes of the depolarization of fluorescence, changes in fluorescence yield, the shape of fluorescence emission spectra, position of fluorescence maxima [4][5][6][7][8][9][10] and many other changes observed when the environment of fluorescing molecule differs [11]. Additionally, the design criteria must be addressed in the development of probes for specific application.…”

Section: Introductionmentioning

confidence: 99%

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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“…Whereas curcumin is a polyphenolic compound with molecular weight 368.39 g/mol and gefitinib is a quinazolamine with molecular weight 446.90 g/mol. Both are the anticancer drug is applicable for various brain and lung cancers.UV spectrophotometric studies revealed that maximum light absorption for Curcumin and Gefitinib are at 423 nm and 254 nm respectively 5,6,7,8 . Hygeia.J.D.Med.9 (1) July 2017; 1-8…”

Section: Introductionmentioning

confidence: 99%

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2017

Hygeia.J.D.Med.

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Effect of hydrogen bonding on the intramolecular charge transfer fluorescence of 6-dodecanoyl-2-dimethylaminonaphtalene

Cited by 48 publications

References 29 publications

Effect of proton-donor solvent and structural flexibility of prodan and laurdan molecules on their spectral-luminescent properties

Effect of proton-donor solvent and structural flexibility of prodan and laurdan molecules on their spectral-luminescent properties

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

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