Fluorine-containing quinoline and quinoxaline styryl derivatives: synthesis and photophysical properties

Носова, Э. В.; Trashakhova, T. V.; Ustyugov, V. S.; Mochul’skaya, N. N.; Валова, М. С.; Lipunova, G. N.; Charushin, Valery N.

doi:10.1007/s11172-011-0148-1

Cited by 10 publications

(5 citation statements)

References 20 publications

(10 reference statements)

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“…The quantum yield of this derivative (6%) is one log lower than with our structure (60%) . Other studies showed as for our structures that electron-withdrawing substituent induced a loss of fluorescence. − …”

Section: Resultssupporting

confidence: 39%

Synthesis of Quinoline Dicarboxylic Esters as Biocompatible Fluorescent Tags

et al. 2012

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A series of dicarboxylic quinoline derivatives bearing electron-releasing or -withdrawing substituents have been synthesized using mono- or/and biphasic methodologies. By controlling the regioselectivity of addition into our electrophilic intermediate, we also characterized by which mechanism the Doebner-Miller cyclization step occurred. As anticipated, electron-releasing substituents induce a red shift of the low-energy absorption allowing excitation in the visible region. In addition, by playing on the strength and position of the electron-releasing substituents, chromophore having interesting fluorescent properties such as large Stoke shifts, good fluorescent quantum yields, emission in the visible green-yellow region and reasonable two-photon absorption in the NIR region have been obtained. These small-size fluorophores, which can be made water-soluble and have been shown to be non-toxic, can be hetero- and/or polyfunctionalized and thus represent promising key units for fluorescence-based physiological experiments with low background interactions.

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Section: Resultssupporting

confidence: 39%

Synthesis of Quinoline Dicarboxylic Esters as Biocompatible Fluorescent Tags

et al. 2012

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“…They are known antiviral agents that are a styrylquinoline inhibitors of HIV integrase [ 1 ], antifungal [ 2 ] and anticancer agents [ 3 ]. Particular attention has been paid to this class of compounds because of their electroluminescence and photochromic properties, which could permit their potential utility in optical devices or as biosensors [ 4 , 5 ]. Many reports have pointed out the feasible use of molecules such as fluorophores that could be suitable for staining intracellular components such as nucleic acids or proteins [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Styrylquinoline Cellular Dyes, Fluorescent Properties, Cellular Localization and Cytotoxic Behavior

et al. 2015

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New styrylquinoline derivatives with their photophysical constants are described. The synthesis was achieved via Sonogashira coupling using the newly developed heterogeneous nano-Pd/Cu catalyst system, which provides an efficient synthesis of high purity products. The compounds were tested in preliminary fluorescent microscopy studies to in order to identify their preferable cellular localization, which appeared to be in the lipid cellular organelles. The spectroscopic properties of the compounds were measured and theoretical TD-DFT calculations were performed. A biological analysis of the quinolines that were tested consisted of cytotoxicity assays against normal human fibroblasts and colon adenocarcinoma cells. All of the compounds that were studied appeared to be safe and indifferent to cells in a high concentration range. The presented results suggest that the quinoline compounds that were investigated in this study may be valuable structures for development as fluorescent dyes that could have biological applications.

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“…However, it can be observed that, as the acceptor strength increases, the emission increases. Generally, a white fluorescence is obtained by mixing three different fluorophores, emitting in the blue, green, and red, or two, one emitting in the blue and the other one in the yellow spectral range [ 19 , 34 ]. A dye emitting over a wide range of colors is thus very attractive from the applicative point of view.…”

Section: Resultsmentioning

confidence: 99%

“…In the work of Nosov et al [ 19 ], it was shown that the lengthening in the conjugation chain in the case of change R substituent displaces the emission band to the region of a longer wavelength. In addition, it causes a transition from blue to green or yellow-orange fluorescence, regardless of the electronic nature of the group introduced.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Studies of Styrylquinoline Copolymers with Different Substituents

et al. 2022

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The aim of the study was to present the influence of various styrylquinoline (StQ) substituents on the luminescence, structural, and optical properties of StQ-containing copolymers. StQ-containing copolymers were synthesized by free-radical thermoinitiated polymerization. The calculations of the copolymerization ratios for the obtained copolymers were based on the basis of the integrated peak areas of the 1H NMR spectra in CDCl3. The luminescence measurements show that the change in the nature of the electron-donating and electron-withdrawing of the substituent shifts the emission band to longer wavelengths and causes a transition from blue fluorescence to green or yellow and orange (or even white), regardless of the electronic nature of the introduced substituent group. The structural properties were measured by Fourier-Transform Infrared (FTIR) and Raman spectroscopies. For all of the compounds, we observed similarities in the bands in FTIR and Raman measurements. The optical parameters were obtained from the absorbance measurements. Additionally, Scanning Electron Microscopy (SEM) was used to study the surface topography of the thin layers on the glass substrate. The SEM images confirm that we obtained smoother layers for two copolymers. The computational Density Functional Theory (DFT) analysis fully supports the beneficial features of the analyzed systems for their applications in optoelectronic devices. Based on the obtained results, it can be concluded that all of the studied styrylquinolines are promising materials for applications in organic light-emitting diodes (OLEDs). However, COP1 with an OCH3 donor substituent possess a wider luminescence band, and its layer is smoother and more transparent.

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Fluorine-containing quinoline and quinoxaline styryl derivatives: synthesis and photophysical properties

Abstract: E) 2 Styryl substituted 6,7 difluoroquinolines and quinoxalines were synthesized by the condensation of the corresponding 2 methylbenzazines with aromatic aldehydes. Photolumines cence of the synthesized 6,7 difluoro 2 styrylbenzazines was studied.

Cited by 10 publications

References 20 publications

Synthesis of Quinoline Dicarboxylic Esters as Biocompatible Fluorescent Tags

Synthesis of Quinoline Dicarboxylic Esters as Biocompatible Fluorescent Tags

Synthesis of New Styrylquinoline Cellular Dyes, Fluorescent Properties, Cellular Localization and Cytotoxic Behavior

Spectroscopic Studies of Styrylquinoline Copolymers with Different Substituents

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