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1.

Вид документа : Статья из журнала
Шифр издания : Г
Автор(ы) : Krinochkin A. P., Mallikarjuna Reddy G., Kopchuk D. S., Slepukhin P. A., Shtaitz Y. K., Khalymbadzha I. A., Kovalev I. S., Kim G. A., Zyryanov G. V., Chupakhin O. N., Charushin V. N., Ganebnykh I. N.
Заглавие : 2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines
Место публикации : Mendeleev Communications. - 2021. - Vol. 31, № 4. - С. 542-544
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 1,2,4-triazines--oxazol-2-amines--diels–alder reaction--2,2'-bipyridin-3-ols
Аннотация: High temperature coupling of 6-aryl-5-cyano-3-(pyridin-2-yl)-1,2,4-triazines with 2-amino-4-aryloxazoles proceeds as the inverse demand Diels–Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene to construct new 4,5-diaryl-6-cyano-3-hydroxypyridin-2-yl fragment. A reaction mechanism is proposed, and the structure of the key-product is proved by the X-ray diffraction analysis.
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2.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Taniya O. S., Fedotov V. V., Sadieva L. K., Krinochkin A. P., Kovalev I. S., Kopchuk D. S., Zyryanov G. V., Ulomsky E. N., Rusinov V. L., Charushin V. N., Novikov A. S., Liu Y.
Заглавие : Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations
Место публикации : Dyes and Pigments. - 2022. - Vol. 204. - Ст.110405
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D−A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (SNH), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm−1. Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow-green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M−1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches.
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3.

Вид документа : Статья из журнала
Шифр издания : Г/A 99
Автор(ы) : Taniya O. S., Khasanov A. F., Varaksin M. V., Starnovskaya E. S., Krinochkin A. P., Savchuk M. I., Kopchuk D. S., Kovalev I. S., Nosova E. V., Zyryanov G. V., Chupakhin O. N., Kim G. A.
Заглавие : Azapyrene-based fluorophores: synthesis and photophysical properties
Место публикации : New Journal of Chemistry. - 2021. - Vol. 45, № 45. - С. 20955-20971
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron–acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of “push–pull” π-conjugated chromophores with pronounced ICT properties. Over the past decade, due to the unrelenting interest in functional materials and modern methodologies such as cross-coupling, peri-annulation, direct C–H-functionalization, etc., methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene.
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4.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Kovalev I. S., Sadieva L. K., Taniya O. S., Yurk V. M., Minin A. S., Kopchuk D. S., Zyryanov G. V., Charushin V. N., Chupakhin O. N.
Заглавие : Bispyrenylalkane chemosensor for the naked-eye detection of nitro-explosives
Место публикации : Chimica Techno Acta. - 2021. - Vol. 8, № 2. - С. 20218209
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): detection of explosives in aqueous media--chemical sensors--fluorescence quenching--pyrene-based fluorophores
Аннотация: Pyrene-based compounds have a great potential as fluorescent chemosensors for various analytes including common nitroexplosives, such as 2,4,6-trinitrotoluene (TNT). Compounds having two pyrene units in one molecule, such as bispyrenylalkanes, are able to form stable, bright emissive in a visual wavelength region excimers both in non-polar and polar environments. In this work we wish to report that in non-polar solvents the excimer has poor chemosensing properties while in aqueous solutions it provides significant “turn-off” fluorescence response to TNT in the subnanomolar concentrations.
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5.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Kovalev I. S., Sadieva L. K., Taniya O. S., Volkova N.N., Minin A. S., Grzhegorzhevskii K. V., Gorbunov E. B., Zyryanov G. V., Chupakhin O. N., Charushin V. N., Tsurkan M. V.
Заглавие : Bola-type pah-based fluorophores/chemosensors: synthesis via an unusual clemmensen reduction and photophysical studies
Место публикации : Journal of photochemistry and photobiology A: Chemistry. - 2021. - Vol. 420. - С. 113466
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
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6.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Kovalev I. S., Sadieva L. K., Taniya O. S., Yurk V. M., Minin A. S., Santra S., Zyryanov G. V., Charushin V. N., Chupakhin O. N., Tsurkan M. V.
Заглавие : Computer vision vs. spectrofluorometer-assisted detection of common nitro-explosive components with bola-type PAH-based chemosensors
Место публикации : RSC Advances. - 2021. - Vol. 11, № 42. - С. 25850-25857
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Computer vision (CV) algorithms are widely utilized in imaging processing for medical and personal electronics applications. In sensorics CV can provide a great potential to quantitate chemosensors' signals. Here we wish to describe a method for the CV-assisted spectrofluorometer-free detection of common nitro-explosive components, e.g. 2,4-dinitrotoluene (DNT) and 2,4,6-trinitrotoluene (TNT), by using polyaromatic hydrocarbon (PAH, PAH = 1-pyrenyl or 9-anthracenyl) – based bola-type chemosensors. The PAH components of these chemical bolas are able to form stable, bright emissive in a visual wavelength region excimers, which allows their use as extended matrices of the RGB colors after imaging and digital processing. In non-polar solvents, the excimers have poor chemosensing properties, while in aqueous solutions, due to the possible micellar formation, these excimers provide “turn-off” fluorescence detection of DNT and TNT in the sub-nanomolar concentrations. A combination of these PAH-based fluorescent chemosensors with the proposed CV-assisted algorithm offers a fast and convenient approach for on-site, real-time, multi-thread analyte detection without the use of fluorometers. Although we focus on the analysis of nitro-explosives, the presented method is a conceptual work describing a general use of CV for quantitative fluorescence detection of various analytes as a simpler alternative to spectrofluorometer-assisted methods.
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7.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Mukherjee A., Kopchuk D. S., Kovalev I. S., Santra S., Varaksin M. V., Zyryanov G. V., Chupakhin O. N., Charushin V. N., Majee A.
Заглавие : Direct C−H functionalization of calix[N](het)arenes (N=4,6): a brief update
Место публикации : ChemistrySelect. - 2022. - Vol. 7, № 12. - С. e202103017
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Calix[n]arenes, their hetero derivatives, are the most popular hosts for the supramolecular and materials chemistry as they can form stable inclusion complexes with charged or neutral molecules, including gases. This short review highlights the most prospective synthetic approaches for direct modification of calix[4]arene core with various functional moieties as well as selected patterns of direct C−H-modification of calix[6]arenes and calix[4]pyrroles.
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8.

Вид документа : Статья из журнала
Шифр издания : 54/E 97
Автор(ы) : Khasanov A. F., Kopchuk D. S., Kovalev I. S., Taniya O. S., Giri K., Slepukhin P. A., Santra S., Rahman M., Majee A., Charushin V. N., Chupakhin O. N.
Заглавие : Extended cavity pyrene-based iptycenes for the turn-off fluorescence detection of RDX and common nitroaromatic explosives
Место публикации : New Journal of Chemistry. - 2017. - Vol. 41, № 6. - С. 2309-2320
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): pyrene (chemical)--fluorescence--rdx (cyclonite)
Аннотация: Extended cavity pyrene-based iptycenes have been synthesized by using the Diels–Alder reaction between in situ generated dehydropyrenes and anthracene. The photophysical properties and the interaction of these iptycenes with nitro-explosive components were studied both in solution and in the solid state by using fluorescence spectroscopy and X-ray crystallography, respectively. Due to the presence of both the large iptycene cavity and the central pyrene core, an unprecedently high fluorescence-quenching response towards non-aromatic and non-planar 1,3,5-trinitroperhydro-1,3,5-triazine (RDX) has been observed both in solution (with an apparent Stern–Volmer constant value aKSV up to 1.53 × 103 M−1) and in the vapor phase (50–75% fluorescence quenching of the PU films doped with chemosensors). In the case of nitroaromatic explosives, nitrobenzene (NB), 2,4-DNT, TNT, and 2,4,6-trinitrophenol (TNP or picric acid, PA), pyrene-based iptycenes also demonstrate a good fluorescence-quenching response both in solutions (with apparent Stern–Volmer constant values aKSV = 0.4–8.0 × 103 M−1) and in the vapor phase (up to 90% fluorescence quenching of the PU films doped with chemosensors). The “sphere of action” fluorescence quenching model was suggested.
\\\\Expert2\\NBO\\New Journal of Chemistry\\2017 v.41 p.2309-2320.pdf
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9.

Вид документа : Статья из журнала
Шифр издания : 54/F 70
Автор(ы) : Kovalev I. S., Taniya O. S., Slovesnova N. V., Kim G. A., Santra S., Zyryanov G. V., Kopchuk D. S., Majee A., Charushin V. N., Chupakhin O. N.
Заглавие : Fluorescent Detection of 2,​4-​DNT and 2,​4,​6-​TNT in Aqueous Media by Using Simple Water-​Soluble Pyrene Derivatives
Место публикации : Chemistry - An Asian Journal. - 2016. - Vol. 11, № 5. - С. 775-781
Примечания : Bibliogr. : p. 780-781 (39 ref.)
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): herbicides--pyrene derivatives--2,4-dnt --2,4,6-tnt
Аннотация: Pyrene-contg. water-sol. probes for the fluorescent detection of nitroarom. compds. (NACs), such as explosive components (2,4-DNT and 2,​4,​6-​TNT) and herbicides (2,4-​dinitrocresol, 2,4-DNOC)​, in aq. media are reported. In the probes, the introduction of surface-​active hydrophilic heads at the periphery of lipophilic (i.e., hydrophobic) pyrene tails resulted in the formation of highly fluorescent micelle-​like aggregates​/pre-​assocs. in aq. solns. at concns. of ≤10-5M. The enhanced fluorescence quenching of the herein reported architectures is achieved in the presence of ultra-​trace amts. of TNT or 2,4-DNT with values of Stern-​Volmer quenching const. close to 1 × 105M and a detection limit as low as 182 ppb. The most hydrophilic probes demonstrated higher response to 2,​4-​DNT over TNT. Filter paper test strips impregnated with 1 × 10-​5M solns. of the probes were able to detect TNT, 2,​4-​DNT, and other NACs at levels as low as 50 ppb in water.
\\\\expert2\\NBO\\Chemistry - an Asian Journal\\2016. 11(5). P. 775-781.pdf
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10.

Вид документа : Статья из журнала
Шифр издания : 54/O-72
Автор(ы) : Kovalev I. S., Kopchuk D. S., Zyryanov G. V., Rusinov V. L., Chupakhin O. N., Charushin V. N.
Заглавие : Organolithium compounds in the nucleophilic substitution of hydrogen in arenes and hetarenes [Электронный ресурс]
Место публикации : Russian Chemical Reviews. - 2015. - Vol. 84, № 12. - С. 1191-1225
Систем. требования: http://iopscience.iop.org/article/10.1070/RCR4462/pdf
Примечания : Bibliogr. : p. 1224-1225 (237 ref.). - 19.01.2016
ББК : 54
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): nucleophilic substitution--hydrogen--arenes and hetarenes
Аннотация: The review considers the most typical examples of the direct non-activated non-catalytic C–C bond formation in arenes and their metal complexes activated by electron-withdrawing substituents in the aromatic nucleus and in hetarenes (azines and their N-oxides, porphyrins, etc.) upon the reactions with aliphatic and (hetero)aromatic (hetero)organolithium nucleophiles. Particular attention is given to the direct introduction of nitroxide radicals and (hetero)organic moieties into mono-, di- and triazines and their N-oxides. The influence of the structures of the (hetero)aromatic substrate and the (hetero)organolithium nucleophile on the reaction pathway and rate and on the structure of the reaction product is analyzed.
\\\\expert2\\nbo\\Russian Chemical Reviews\\2015, V.84, N12, p. 1191-1225.pdf
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