Solvent effects on electronic transitions of fluorenone and 4-hydroxyfluorenone

Józefowicz, Marek; Heldt, J.

doi:10.1016/j.chemphys.2005.10.028

Cited by 37 publications

(18 citation statements)

References 12 publications

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“…The latter results from the short-range interactions between the fluorophore and solvent molecules in its first solvation shell such as hydrogen bonding. 5 Hydrogen bonds between a protic solvent and a fluorescent molecule may form under certain conditions, which can considerably affect the molecular orbital energy levels and accordingly influence the photophysical properties. 6 As a fluorescent dyes with high stability and strong intensity, naphthalic anhydrides and their derivatives have wide range of applications.…”

Section: Introductionmentioning

confidence: 99%

Determination of Water Content in Organic Solvents by Naphthalimide Derivative Fluorescent Probe

Niu

Qin

et al. 2010

ANAL. SCI.

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Section: Introductionmentioning

confidence: 99%

Determination of Water Content in Organic Solvents by Naphthalimide Derivative Fluorescent Probe

Niu

Qin

et al. 2010

ANAL. SCI.

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“…It is well-known that the solvent can influence the physicochemical properties of a solute in a wide variety of chemical processes [35][36][37][38][39]. In order to explore the role of solute-solvent interactions and intramolecular torsion motions i.e., flexibility of the studied molecule, the reorganization energy for EDMAADCy has been determined as a function of solvent polarity.…”

Section: Determination Of Reorganization Energy Of Edmaadcy In Neat Smentioning

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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“…The literature contains numerous investigations that make use of the Kamlet-Taft and/or Catal an models in order to explain the effects of pure solvents and solvent mixtures on the photophysical properties of molecules and to demonstrate the role of excited-state H-bonds [55][56][57][58][59][60][61]. Some examples of studies employing the Kamlet-Taft model are presented in Table 4.2. Aaron et al [66] correlated the values/signs of the estimated Kamlet-Taft coefficients with the trends of the experimental spectra of a series of fused benzothiophenes.…”

Section: Solvatochromic Analysismentioning

confidence: 99%

“…In the case of fluorenone, the presence in alcohols of H-bonds implicating the oxygen of the carbonyl group was extensively reported [60,[84][85][86][125][126][127]. However, the related ketone benzo[b]fluorenone was not quenched by alcohols [128], and H-bond formation was observed only in the strong HBD solvent TFE.…”

Section: Selection Of Solventsmentioning

confidence: 99%

Solute–Solvent Hydrogen Bond Formation in the Excited State. Experimental and Theoretical Evidence

Matei

Ionescu

Hillebrand

2010

Hydrogen Bonding and Transfer in the Excited State

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Hydrogen bonds (H-bonds) are of great importance in biological systems, as they are responsible for the secondary structure of proteins and nucleic acids and are also involved in the mechanisms of enzyme catalysis. Supramolecular chemistry makes use of H-bonds in building up novel compounds of various architectures.The identification of these interactions and the analysis of their influence on the photophysical properties are also important in designing new fluorophores for different applications, the processes involved being rather complex in nature and often only partially understood.The main feature reflecting H-bond interaction in both the ground and excited states is the solvatochromic effect on the absorption and fluorescence spectra. This implies that changes in the solvent nature or composition produce shifts in the position, shape and intensity of the spectral bands. The source of solvatochromic shifts is the different solvation of the ground and excited states: depending on the relative stabilization of these states by solvents, bathochromic (positive)or hypsochromic (negative)shifts of the maximum of the band can be observed experimentally. Thus, such changes are indicative of the interactions occurring between the solute and the solvent in its immediate vicinity. The solute-solvent interactions are classified into:1. non-specific interactions caused by polarity/polarizability effects; 2. specific interactions, such as H-bonds.

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Solvent effects on electronic transitions of fluorenone and 4-hydroxyfluorenone

Cited by 37 publications

References 12 publications

Determination of Water Content in Organic Solvents by Naphthalimide Derivative Fluorescent Probe

Determination of Water Content in Organic Solvents by Naphthalimide Derivative Fluorescent Probe

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

Solute–Solvent Hydrogen Bond Formation in the Excited State. Experimental and Theoretical Evidence

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