Solvent effects on the absorption/emission spectra of an organic chromophore: A theoretical study

Clemens, Oliver; Basters, Matthias; Wild, Mandy; Wilbrand, Sabine; Reichert, Christian; Bauer, Michael; Springborg, Michael; Jung, Gregor

doi:10.1016/j.theochem.2008.06.028

Cited by 17 publications

(13 citation statements)

References 11 publications

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“…The plausible argument is the hypothesis of another electronic distribution resulting from the solvation of the molecule. These results are in the line with the observations of Clemens et al [51] on some organic chromophores. Accordingly, ESI ‡, Fig.…”

Section: Geometrical Detailssupporting

confidence: 94%

Thermodynamics-antioxidant activity relationships of some 4-benzylidenamino-4, 5-dihydro-1h-1,2,4-triazol-5-one derivatives: Theoretical evaluation

Mfomo

Mama

Lissouck

et al. 2017

International Journal of Food Properties

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Density functional methods were used to predict the antioxidative efficiency of thirteen 4-benzylidenamino-4, 5-dihydro-1H-1,2,4-triazol-5-one derivatives in the gas phase and in the solution phase (water and benzene). Optimized geometries of molecules and reaction thermodynamic energies (enthalpies and reaction-free energies) of three main antioxidant mechanisms (hydrogen atom transfer, single electron transfer-proton transfer, and sequential proton loss electron transfer) were studied at B3LYP/6-31G (d,p) level. Solvent contributions to thermodynamic energies were computed employing integral equation formalism integral equation formalism polarized continuum model method. Obtained results revealed that the three main working mechanisms were endothermic, but not spontaneous especially in the gas phase. We found that the single electron transfer process from the anionic form was more preferable than that from the neutral form in the gas phase. The comparison of the ionization potentials of 4-benzylidenamino-4, 5-dihydro-1H-1,2,4-triazol-5-one derivatives to those of classical antioxidants (gallic acid, caffeic acid, ferulic acid, and ascorbic acid) indicated that the electron transfer mechanism was more predominant in the thirteen 4-benzylidenamino-4, 5-dihydro-1H-1,2,4-triazol-5-one derivative compounds. Thermodynamically, single electron transfer process from the anionic form was the most preferable mechanism in the gas phase. Solvent effect drastically modified thermodynamic energies of mechanisms. The proton transfer process was the thermodynamically favored mechanism as compared to other mechanisms in both solvents. It is worth mentioning that all the mechanisms were found not to be spontaneous in the solution phase except the proton transfer process.

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Section: Geometrical Detailssupporting

confidence: 94%

Thermodynamics-antioxidant activity relationships of some 4-benzylidenamino-4, 5-dihydro-1h-1,2,4-triazol-5-one derivatives: Theoretical evaluation

Mfomo

Mama

Lissouck

et al. 2017

International Journal of Food Properties

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“…Replacing the terminal ferrocene unit with a phenyl ring14 has the effect of transforming the absorption spectrum into that characteristic of the Bodipy π‐electron framework; the maximum ( λ max ) occurs at 571 nm, there is a vibronic progression of about 1200 cm −1 and the band half‐width (FWHM) is reduced to about 900 cm −1 . The corresponding compound with a terminal 4‐( N , N ‐dimethylamino) unit,15 this being a better electron donor than a simple phenylene ring, pushes λ max out to 605 nm and broadens the spectrum considerably (FWHM=1,905 cm −1 ) due to the introduction of charge‐transfer character. Protonation restores the “normal” absorption spectral properties,3 with λ max being 554 nm and FWHM falling to 815 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

Boron Dipyrrin Dyes Exhibiting “Push–Pull–Pull” Electronic Signatures

Ziessel

Retailleau²,

Elliott

et al. 2009

Chemistry A European J

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Manipulating the electronic pathway: A strategy has been devised for functionalizing boron dipyrrin dyes with one or two electroactive ferrocene units at the periphery. Oxidation of one or both ferrocene residues is fully reversible and gives rise to near‐IR electrochromism. One‐electron oxidation of the bis‐derivative transforms the original “push–pull–push” system into a “push–pull–pull” signature.

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“…3(a) suggests that the fluorescence spectra of 2b in chloroform, and to some extend in DMSO as well, shows timedependent fluorescent intensities. In contrast, most solvatochromic BODIPY fluorophores that have been reported in the literature often show different maximal emission wavelengths (Baruah et al, 2006;Clemens et al, 2008;Filarowski et al, 2010Filarowski et al, , 2015de Rezende et al, 2014), however, those solvatochromic BODIPY dyes do not display a time-dependent change in fluorescent intensity.…”

Section: Solvent-dependent Behaviour Of Bodipy 2b Observed By Nmr Spementioning

confidence: 99%

Crystal structure and solvent-dependent behaviours of 3-amino-1,6-diethyl-2,5,7-trimethyl-4,4-diphenyl-3a,4a-diaza-4-bora-s-indacene

Yang¹,

Drew²,

Yalagala³

et al. 2017

Acta Cryst E

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Solvent effects on the absorption/emission spectra of an organic chromophore: A theoretical study

Cited by 17 publications

References 11 publications

Thermodynamics-antioxidant activity relationships of some 4-benzylidenamino-4, 5-dihydro-1h-1,2,4-triazol-5-one derivatives: Theoretical evaluation

Thermodynamics-antioxidant activity relationships of some 4-benzylidenamino-4, 5-dihydro-1h-1,2,4-triazol-5-one derivatives: Theoretical evaluation

Boron Dipyrrin Dyes Exhibiting “Push–Pull–Pull” Electronic Signatures

Crystal structure and solvent-dependent behaviours of 3-amino-1,6-diethyl-2,5,7-trimethyl-4,4-diphenyl-3a,4a-diaza-4-bora-s-indacene

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