Organic luminophores with fluorine-containing substituents

Krasovitskii, B. M.; Pereyaslova, D. G.; Skripkina, V. T.; Yagupol’skii, L. M.; Попов, В. И.

doi:10.1016/0143-7208(88)85002-2

Cited by 10 publications

(4 citation statements)

References 1 publication

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“…The low fluorescence of our pyrazolines was atypical of this group of organic compounds. Substitution on the phenyl radical in position 5 of the pyrazolines of the 5a-g series (fragment b, Scheme 2) did not increase luminescence because fragment b is not conjugated with the main chromophore (Kimura et al, 1977), although there are reports of adverse effects of the substitution at carbon 5 in the pyrazolinic ring on fluorescence; the fluorescence of pyrazolines decreases with -electron conjugated systems or SO2X type substituents at position 5 where Х is a methyl fluoride group (Krasovitskii et al, 1988). This decrease in fluorescence may be due to competition between fluorescence and intersystem crossing (Svinarev et al, 1990), a radiationless relaxation crossover between electronic states of different multiplicity.…”

Section: Fluorescence and Intersystem Crossingmentioning

confidence: 99%

“…In the conjugated chain -N 1 -N 2 =C 3 -of the pyrazoline ring, N 1 and C 3 are electron donating and withdrawing atoms, respectively; the carbon atom at position 5 does not conjugate with this chain; therefore, changing the substituents attached to this carbon atom should have only a small effect on the photophysical properties of pyrazolines and changing the groups attached to the 1-or 3-carbon atoms, should change these properties (Zhang et al, 2000). Nevertheless, there is also evidence that substitution in position 5 affected fluorescence (Krasovitskii et al, 1988).…”

Section: Introductionmentioning

confidence: 99%

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1,3,5-Triaryl 2-Pyrazolines With 8-Hydroxyquinolinic Substituent: Syntheses, Photophysical Properties, and Biological Activity

Marrugo-González¹,

Orlov²,

Fernandez‐Maestre³

2015

PTQ

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1,3,5-triaryl-2-pyrazolines are organic luminophores with arylic radicals that show a wide biological activity and are used as liquid scintillators and electro-optic materials. Experimental. Eleven 2-pyrazolines were synthesized from phenylhidrazine and chalcones of the 8-hydroxyquinoline series: 3-(8-hydroxyquinolin-5-yl)-1-(3-R)-phenylprop-2-enone and 1-(8-hydroxyquinolin-5-yl)-3--(3-R)-phenylprop-2-enone, where R = H, CH3, OCH3, N(CH3)2, Cl, Br, and NO2. The structures were confirmed by elemental analysis, IR, 1H-NMR, and electronic spectroscopy. Results and discussion. The 1- and 3-aryl substituents of the pyrazoline ring produced shifts to shorter or longer wavelengths, in absorbance and fluorescence. The electron acceptor hydroxyquinolinic fragment influenced the absorption and luminescence spectra; the possible cause of low quantum yields in pyrazolines (1-phenyl-3-(4-R phenyl)-5-(8-hydroxyquinolinil-5)-2-pyrazoline) may be the specific intramolecular fluorescence quenching in bicromophores, characteristic of 5-acceptor substituted pyrazolines, and, in series (1-phenyl-5-(4-R phenyl)-3-(8-hydroxyquinolinil-5)-2-pyrazoline) of excited-state intramolecular proton transfer (ESIPT) reactions, and the increasing donor-acceptor intramolecular interaction of their excited molecules; Density functional calculations (method PM6) were used to probe the electronic structure and energy ordering of the emissive and the electron-transfer states; PM6 results agreed with the experimental data. 1-phenyl-3-(4-R phenyl)-5-(8-hydroxyquinolinil-5)-2-pyrazoline showed fungistatic and fungicide activities. Additionally, all our pyrazolines showed wide theoretical biological activities.

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Section: Fluorescence and Intersystem Crossingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

1,3,5-Triaryl 2-Pyrazolines With 8-Hydroxyquinolinic Substituent: Syntheses, Photophysical Properties, and Biological Activity

Marrugo-González¹,

Orlov²,

Fernandez‐Maestre³

2015

PTQ

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“…Several authors have investigated the luminescence properties of azlactones and very low fluorescence efficiencies have been reported for solutions in different solvents (Krasovitskii 1988). Under the light of the literature, one would study the fluorescence emission of azlactone molecule in an immobilized phase, where higher yield of fluorescence emission and improved stability toward chemical and photochemical environment could be reached (Icli 1999).…”

Section: Introductionmentioning

confidence: 99%

Optical Determination of Glucose with Glucose Oxidase Immobilized in PVC together with Fluorescent Oxazol‐5‐One Derivatives

Ozturk

Tımur²,

Alp

2008

Analytical Letters

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Fully reversible biosensors for glucose monitoring based on solid polyvinylchloride (PVC) films where the enzyme glucose oxidase (GOx) was incorporated together with 2-phenyl-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadec yl)benzylidene]-5-oxazolone (CPO-1), 2-(3,5-dinitrophenyl)-4-[4-(1,4,7,10-tetra oxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-2), 2-(4-nitrophenyl) -4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-3) and 2-(4-tolyl)-4-[4-(1,4,7,10-tetraoxa-13-azacyclopentadecyl)benzylidene]-5-oxazolone (CPO-4) derivatives have been developed. The limit of detection (LOD) values for glucose were found to be 1.47 Â 10 25 M, 2.01 Â 10 25 M, 0.89 Â 10 25 M, and 0.12 Â 10 25 M for CPO-1, CPO-2, CPO-3, and CPO-4, respectively (n ¼ 7). Sensor films were found to have excellent photostability.

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“…Here we do not consider the last possibility, because in such a case 5-aryl moiety is out of conjugation with the main chromophoric fragment of the molecule, 1,3-diaryl-2-pyrazoline. In most cases substituents in position 5 of pyrazoline cycle have no effect on fluorescent characteristics at all, however, several publications reported dramatic decreasing of fluorescence quantum yields in case of introducing into position 5 electron-withdrawing groups or polycyclic aromatic moieties like anthracene [37][38][39][40].…”

Section: Introductionmentioning

confidence: 99%

1,5-Diaryl-3-Benzimidazolyl-2-Pyrazolines and Pyrazoles – Novel Fluorescent Dyes of Pyrazoline Family

Kotlyar¹,

Orlov²,

Grygorovych³

et al. 2017

Chemical Series

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A series of novel aryl derivatives of 2-pyrazoline bearing 2-benzimidazolyl moiety was synthesized via condensation of corresponding chalcones with phenyl hydrazine. Pyrazoles on their background were obtained by the optimized oxidation procedure with manganese dioxide in benzene. Fluorescent characteristics of the title compounds were determined for their solutions in acetonitrile. Quantum-chemical modeling of molecular structure, UV/Vis spectra, electron density redistribution and structural relaxation at electronic excitation resulting in high fluorescence Stokes shifts were conducted as well.

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Organic luminophores with fluorine-containing substituents

Cited by 10 publications

References 1 publication

1,3,5-Triaryl 2-Pyrazolines With 8-Hydroxyquinolinic Substituent: Syntheses, Photophysical Properties, and Biological Activity

1,3,5-Triaryl 2-Pyrazolines With 8-Hydroxyquinolinic Substituent: Syntheses, Photophysical Properties, and Biological Activity

Optical Determination of Glucose with Glucose Oxidase Immobilized in PVC together with Fluorescent Oxazol‐5‐One Derivatives

1,5-Diaryl-3-Benzimidazolyl-2-Pyrazolines and Pyrazoles – Novel Fluorescent Dyes of Pyrazoline Family

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