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8. Two-step synthesis of new fused systems based on [1,2,5]oxadiazolo[3,4-b]quinoxaline by a combination of the Scholl reaction and nucleophilic aromatic substitution of hydrogen (SNH).

Author

Krynina, E. M., Kvashnin, Yu. A., Gazizov, D. A., Kodess, M. I., Ezhikova, M. A., Rusinov, G. L., Verbitskiy, E. V., and Charushin, V. N.

Subjects
NUCLEOPHILIC substitution reactions, ORGANIC semiconductors, QUINOXALINES, ENERGY levels (Quantum mechanics), N-type semiconductors
Abstract

A simple synthetic route to poorly available polycyclic systems with a [1,2,5]oxadiazolo-[3,4-b]quinoxaline backbone has been developed, which is based on the sequence of nucleophilic aromatic substitution of hydrogen and the Scholl cross-coupling. According to the data from electrochemical and photophysical measurements, the synthesized compounds can be potentially considered as the narrow-gap (from 1.97 to 2.34 eV) n-type organic semiconductors, the energy levels of which are comparable to those of top commercially available electronic semiconductors. [ABSTRACT FROM AUTHOR]

Published
2024
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11. ФЛУОРЕСЦЕНТНОЕ ОПРЕДЕЛЕНИЕ ПАРОВ НИТРОБЕНЗОЛА С ИСПОЛЬЗОВАНИЕМ ДОПИРОВАННОГО ФЛУОРОФОРАМИ ПОЛИСТИРОЛА

Author

Chuvashov, R. D., Belyaev, D. V., Khokhlov, K. O., Baranova, A. A., Zen Eddin, M., Milman, I. I., Verbitskiy, E. V., The reported study was funded by RFBR, project number 20-37-90108, and Исследование выполнено при финансовой поддержке РФФИ в рамках научного проекта № 20-37-90108.

Abstract

Integration of fluorescent substances into polymeric matrices can improve their sensory properties and photostability. In this work, fluorescent materials based on fluorophore-doped polystyrene were obtained and characterized as sensors towards the ecotoxicant nitrobenzene in gas phase. Melamine-formaldehyde foam has been proposed as a permeable substrate for the sensor material deposition applicable for gas-phase measurements. The effect on sensor properties of the porous material surface obtained via Breath Figure pore generation technique was investigated. Limits of detection and calibration relationships of obtained materials towards nitrobenzene were evaluated by materials exposure to low concentrations of nitrobenzene vapors. The sorption properties of polystyrene allow the retention of the quencher near the fluorophore, leading to improved detection limits compared with pure fluorophores. Obtaining a porous surface of the polymer material by the Breath Figure technique increases the scale of its fluorescence quenching by vapors. Detection limits (down to 0.45 ppm) and detectable concentration ranges (0.5 - 371.6 ppm) have been experimentally established. The relative standard deviations of the fluorescent signal of polymer materials do not exceed 13.3 % for a number of concentrations in the detectable range. The applicability of the calibration linear relationship of the logarithm of the fluorescent signal on the logarithm of the nitrobenzene vapor concentration is shown. Fluorescence signal measurements were performed using the original sensor element and the luminescence detector employing an array of fluorescent materials. The developed device is simple in application, portable, automated, and in combination with the used polymeric materials allows detection of nitrobenzene vapors in concentrations 2.5 times lower than the maximum permissible level. Keywords: Fluorescence, nitrobenzene, polystyrene, melamine, doping, breath figure, fluorescence reader, Интеграцией флуоресцентных веществ в полимерные матрицы можно улучшить их сенсорные свойства и фотостабильность. В работе получены и исследованы флуоресцентные материалы на основе допированного флуорофорами полистирола в качестве сенсоров на экотоксикант нитробензол в газовой фазе. Меламин-формальдегидная пена предложена в качестве проницаемого субстрата для нанесения сенсорных составов. Исследовано влияние техники создания пористой поверхности материала Breath Figure на сенсорные свойства. Пределы обнаружения нитробензола в газовой фазе с использованием полученных материалов были оценены экспозицией малым концентрациям паров нитробензола. Измерения флуоресцентного сигнала были выполнены с помощью оригинальных сенсорного элемента и регистратора люминесценции, применяющих комбинацию флуоресцентных материалов. Разработанное техническое решение регистратора люминесценции является простым в применении, портативным, автоматизированным и позволяет с использованием полученных полимерных материалов обнаружение паров нитробензола в концентрациях ниже предельно допустимой по гигиеническим нормативам.

Published
2023

13. Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts

Author

Verbitskiy, E. V., Le Poul, P., Bureš, F., Achelle, S., Barsella, A., Kvashnin, Y. A., Rusinov, G. L., Charushin, V. N., Verbitskiy, E. V., Le Poul, P., Bureš, F., Achelle, S., Barsella, A., Kvashnin, Y. A., Rusinov, G. L., and Charushin, V. N.

Abstract

A series of novel V-shaped quinoxaline, [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thia-diazolo[3,4-b]pyrazine push–pull derivatives with 2,4′-biphenylene linker were designed and their electrochemical, photophysical and nonlinear optical properties were investigated. [1,2,5]Oxadia-zolo[3,4-b]pyrazine is the stronger electron-withdrawing fragment as shown by electrochemical, and photophysical data. All compounds are emissive in a solid-state (from the cyan to red region of the spectrum) and quinoxaline derivatives are emissions in DCM solution. It has been found that quinoxaline derivatives demonstrate important solvatochromism and extra-large Stokes shifts, characteristic of twisted intramolecular charge transfer excited state as well as aggregation induced emission. The experimental conclusions have been justified by theoretical (TD-)DFT calculations. © 2022 by the authors. Li-censee MDPI, Basel, Switzerland.

Published
2022

14. Fluorometric Determination of Chloramphenicol in Aqueous Solutions Using Acetylene Derivatives of Carbazole, Anthracene and Pyrene

Author

Kozyrina, Yu. V., Zaidullina, R. A., Svalova, T. S., Kozitsina, A. N., Kvashnin, Yu. A., and Verbitskiy, E. V.

Subjects
КАРБАЗОЛ, ФЛУОРЕСЦЕНТНЫЙ АНАЛИЗ, FLUORESCENCE ANALYSIS, АНТРАЦЕН, CHLORAMPHENICOL, ХЛОРАМФЕНИКОЛ, ПИРЕН, PYRENE, CARBAZOLE, ANTHRACENE
Abstract

Определение следовых количеств антибиотиков в воде и пище является актуальной задачей современного экологического мониторинга. Настоящее исследование посвящено оценке возможностей флуорометрического определения хлорамфеникола в водных растворах с использованием в качестве сенсорных молекул ацетиленпроизводных карбазола, антрацена и пирена. Показано закономерное снижение интенсивности флуоресценции, обусловленное процессами супрамолекулярного взаимодействия исследуемых флуорофоров с аналитом. Наибольшие перспективы дальнейшего аналитического применения продемонстрировало соединение на основе карбазола, показав в широком линейном диапазоне (0,1-25 мкМ) высокую чувствительность Ksv=17214 M-1 с пределом обнаружения в 1,09 мкМ. Determination of trace amount of antibiotics in water and food is an actual task of modern environmental monitoring. The present research is devoted an assessment of the possibilities of fluorometric determination of chloramphenicol in aqueous solutions using acetylene derivatives of carbazole, anthracene and pyrene as sensory molecules. A regular decrease in the intensity of fluorescence is shown conditioned by processes of supramolecular interaction of the studied fluorophores with analyte. The greatest prospects for further analytical application demonstrated by the carbazole-based compound, showing in a wide linear range (0,1-25 μM) a high sensitivity of Ksv=17214 M-1 with a detection limit 1,09 μM. Исследование выполнено при финансовой поддержке Совета по грантам Президента РФ проект МК-392.2022.1.3

Published
2022

26. V-Shaped Methylpyrimidinium Chromophores for Nonlinear Optics

Author

Achelle, S., Verbitskiy, E. V., Fecková, M., Bureš, F., Barsella, A., Robin-le, Guen, F., Achelle, S., Verbitskiy, E. V., Fecková, M., Bureš, F., Barsella, A., and Robin-le, Guen, F.

Abstract

A series of four V-shaped methylpyrimidinium salts bearing diphenylamino-electron-donating groups appended at various pyrimidine positions were designed. These chromophores were obtained by regioselective N(1) monomethylation by methyl methanesulfonate of the pyrimidine core. Linear optical properties were studied experimentally and electronic properties were further completed by (TD)-DFT calculations. The second-order nonlinear optical (NLO) properties were also studied using electric field induced second harmonic generation (EFISH) method in chloroform, and all pyrimidinium salts exhibited μβ0>1000×10−48 esu. The 2,4-disubstituted pyrimidinium core is preferred over 4,6-disubstitution as it enhances the NLO response and increases the dipole moment. (E,E)-2,4-Bis[4-(diphenylamino)styryl]-1-methylpyrimidin-1-ium methanesulfonate appears to be the best NLO-phore in chloroform in the series (μβ0=2500×10−48 esu) and a figure of merit μβ0/MW=3.4 10−48 esu mol g−1. © 2021 Wiley-VCH GmbH

Published
2021

27. Synthesis, photophysical and nonlinear optical properties of [1,2,5]oxadiazolo[3,4-b]pyrazine-based linear push-pull systems

Author

Verbitskiy, E. V., Achelle, S., Bureš, F., le, Poul, P., Barsella, A., Kvashnin, Y. A., Rusinov, G. L., Guen, F. R. -L., Chupakhin, O. N., Charushin, V. N., Verbitskiy, E. V., Achelle, S., Bureš, F., le, Poul, P., Barsella, A., Kvashnin, Y. A., Rusinov, G. L., Guen, F. R. -L., Chupakhin, O. N., and Charushin, V. N.

Abstract

A series of D-π-A chromophores based on [1,2,5]oxadiazolo[3,4-b]pyrazine electron-withdrawing group has been designed. The influence of the π-conjugated linker (1,4-phenylene and 2,5-thienylene) and the amino-electron-donating group (diphenylamino and carbazol-9-yl) was studied by cyclic voltammetry, UV-Vis and emission spectroscopy. The second order nonlinear optical properties were also studied using the electric field induced second harmonic generation (EFISH) method. The experimental results have been rationalized by theoretical DFT calculations. © 2020 Elsevier B.V.

Published
2021

29. INKJET PRINTING FOR FABRICATION OF SENSORS FOR NITROCOMPOUND DETECTION

Author

Chuvashov, R. D., Verbitskiy, E. V., Khokhlov, K. O., and Baranova, A. A.

Abstract

Results of the study on fabrication of nitrocompound sensor with use of inkjet printing is discussed. Results are evaluated on experimental stands for liquid and vapor phase applica-tions.

Published
2020

30. Azaheterocyclic push-pull chromophores: synthesis, photophysical properties and applications as fluorescent sensors

Author

Verbitskiy, E. V., Rusinov, G. L., Chupakhin, O. N., and Charushin, V. N.

Subjects
PUSH-PULL FLUOROPHORES, PYRAZINE, FLUORESCENCE QUENCHING, PYRIMIDINE
Abstract

The recently obtained data on functionalization of pyrimidine [1–9] and pyrazine [10–12] derivatives by Suzuki or transition metal-free cross-coupling reactions will be presented. Due to the significant π-deficient character of azaheterocyclic moiety, they can be used as electron-withdrawing group in push-pull structures in which intramolecular charge transfer process occurs (figure). The photophysical properties for such fluorophores have been investigated using absorption and emission spectral analyses, both in solution and in solid-state. Some dyes exhibit strong emission solvatochromism (up to 200 nm) and possess high quantum yields, depending on their molecular structure and solvent polarity. Meanwhile, fluorescence studies have shown that emission of this fluorophores is sensitive towards various nitroaromatic compounds, either in solutions or in a vapor phase. Thus, these compounds can be regarded as promising multifunctional chemosensors. This work was supported by the Russian Foundation for Basic Research (Research Project № 18-29-23045 мк).

Published
2020

32. Dibenzo[ f,h]furazano[3,4- b]quinoxalines: Synthesis by Intramolecular Cyclization through Direct Transition Metal-Free C-H Functionalization and Electrochemical, Photophysical, and Charge Mobility Characterization

Author

Kvashnin, Y. A., Verbitskiy, E. V., Eltsov, O. S., Slepukhin, P. A., Tameev, A. R., Nekrasova, N. V., Rusinov, G. L., Nunzi, J. -M., Chupakhin, O. N., Charushin, V. N., Kvashnin, Y. A., Verbitskiy, E. V., Eltsov, O. S., Slepukhin, P. A., Tameev, A. R., Nekrasova, N. V., Rusinov, G. L., Nunzi, J. -M., Chupakhin, O. N., and Charushin, V. N.

Abstract

Herein, we describe the synthesis of unsymmetrically substituted dibenzo[f,h]furazano[3,4-b]quinoxalines by intramolecular cyclization through direct transition metal-free C-H functionalization. The electrochemical and photophysical properties for several polycycles have been measured. In thin films of the dibenzo[f,h]furazano[3,4-b]quinoxalines, hole mobility is in the order of 10-4 cm2 V-1 s-1. The results show that the HOMO and LUMO energy levels are appropriate for using the compounds as hole-transport materials in thin-film devices, in particular, organic and perovskite solar cells. Copyright © 2020 American Chemical Society.

Published
2020

33. Synthesis of Heteroannulated Indolopyrazines through Domino N-H Palladium-Catalyzed/Metal-Free Oxidative C-H Bond Activation

Author

Kvashnin, Y. A., Verbitskiy, E. V., Zhilina, E. F., Rusinov, G. L., Chupakhin, O. N., Charushin, V. N., Kvashnin, Y. A., Verbitskiy, E. V., Zhilina, E. F., Rusinov, G. L., Chupakhin, O. N., and Charushin, V. N.

Abstract

A convenient approach to [1,2,5]oxadiazolo[3′,4′:5,6]pyrazino[2,3-b]indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald-Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured. © 2020 American Chemical Society.

Published
2020

34. New Approach to Unsymmetrical 1,3- and 1,4-Diazatriphenylene Derivatives Through Intramolecular Oxidative Cyclodehydrogenation

Author

Pakhomov, I. M., Verbitskiy, E. V., Kvashnin, Yu. A., Tameev, A. R., Rusinov, G. L., Chupakhin, O. N., and Charushin, V. N.

Abstract

The research was financially supported by the Russian Science Foundation (Project № 16-13-10435). NMR spectra and elemental analyses were covered by Program of the Ural Branch of the Russian Academy of Sciences (Рroject № 18-3-3-12).

Published
2019

35. New V-shaped 2,4-di(hetero)arylpyrimidine push-pull systems: Synthesis, solvatochromism and sensitivity towards nitroaromatic compounds

Author

Verbitskiy, E. V., Dinastiya, E. M., Baranova, A. A., Khokhlov, K. O., Chuvashov, R. D., Yakovleva, Y. A., Makarova, N. I., Vetrova, E. V., Metelitsa, A. V., Slepukhin, P. A., Rusinov, G. L., Chupakhin, O. N., Charushin, V. N., Verbitskiy, E. V., Dinastiya, E. M., Baranova, A. A., Khokhlov, K. O., Chuvashov, R. D., Yakovleva, Y. A., Makarova, N. I., Vetrova, E. V., Metelitsa, A. V., Slepukhin, P. A., Rusinov, G. L., Chupakhin, O. N., and Charushin, V. N.

Abstract

Novel D–π–A–π–D type pyrimidine-based dyes, possessing (hetero)aryl electron-donating groups in 2,4-positions were synthesized, and their photophysical properties were investigated by using absorption and emission spectral analyses. All dyes proved to exhibit a strong emission solvatochromism with quantum yields up to 0.96, depending on their molecular structure and solvent polarity. The compounds have been established to undergo a reversible protonation, directed at nitrogen atoms of the pyrimidine ring, and these phenomena are associated with dramatic color changes. In addition, fluorophores 5a-d show a high sensitive response for nitroaromatic traces in solutions or real-time detection of their vapors in air. These findings indicate that the compounds obtained can be regarded as excellent fluorophores for fluorescent material applications. © 2018 Elsevier Ltd

Published
2018

36. Diazatriphenylenes and their thiophene analogues: Synthesis and applications

Author

Verbitskiy, E. V., Rusinov, G. L., and Charushin, V. N.

Subjects
PYRAZINES, PYRIDAZINES, DIAZANAPHTHALENES, PYRIMIDINES, TRIPHENYLENES, PHENANTHRENO[9,10-B]THIOPHENE
Abstract

This review highlights the recent advances in the field of the synthesis of diazatriphenylenes and their structural analogues, such as phenanthrenes, fused with the thiophene ring, and naphthalenes, condensed with two thiophene rings. Also applications of these compounds are considered. © ARKAT USA, Inc. The research was financially supported by the Russian Science Foundation (Project No. 16-13-10435) and the Russian Foundation for Basic Research (research project №. 17-03-00011-А).

Published
2017

39. Microwave-Assisted synthesis and evaluation of antibacterial activity of novel 6-fluoroaryl-[1,2,4]triazolo[1,5-A]pyrimidines

Author

Verbitskiy, E. V., Baskakova, S. A., Rasputin, N. A., Gerasimova, N. A., Amineva, P. G., Evstigneeva, N. P., Zil'berberg, N. V., Kungurov, N. V., Kravchenko, M. A., Skornyakov, S. N., Rusinov, G. L., Chupakhin, O. N., Charushin, V. N., Verbitskiy, E. V., Baskakova, S. A., Rasputin, N. A., Gerasimova, N. A., Amineva, P. G., Evstigneeva, N. P., Zil'berberg, N. V., Kungurov, N. V., Kravchenko, M. A., Skornyakov, S. N., Rusinov, G. L., Chupakhin, O. N., and Charushin, V. N.

Abstract

A series of 6-fluoroaryl substituted [1,2,4]triazolo[1,5-A]pyrimidines have been synthesized by using the microwave-Assisted Suzuki cross-coupling reaction from readily available 6-bromo-[1,2,4]triazolo[1,5-A]pyrimidine. The antimicrobial activity of new compounds has been evaluated in vitro against Mycobacterium tuberculosis H37Rv and gram-negative (Neisseria gonorrhoeae ATCC 49226) bacteria. © ARKAT-USA, Inc.

Published
2016

40. Synthesis, X-ray crystal structure and antimycobacterial activity of enantiomerically pure 1-ethyl-2,3-dicyano-5-(het)aryl-6-hetaryl-1,6- dihydropyrazines

Author

Verbitskiy, E. V., Toporova, M. S., Kodess, M. I., Ezhikova, M. A., Isenov, M. L., Pervova, M. G., Kravchenko, M. A., Medvinskiy, I. D., Skornyakov, S. N., Rusinov, G. L., Charushin, V. N., Verbitskiy, E. V., Toporova, M. S., Kodess, M. I., Ezhikova, M. A., Isenov, M. L., Pervova, M. G., Kravchenko, M. A., Medvinskiy, I. D., Skornyakov, S. N., Rusinov, G. L., and Charushin, V. N.

Abstract

The Petasis reaction of 6-alkoxy adducts of 1-alkyl-2,3-dicyano-5- arylpyrazinium salts with aromatic boronic acids, such as 2-thienylboronic, 2-furanylboronic and 3-thienylboronic acids, or their benzo analogs in dichloromethane proceeds smoothly at room temperature with the formation of the corresponding 5-aryl-6-hetaryl substituted 1,6-dihydropyrazine derivatives. All dihydropyrazines were separated as pure enantiomers by chiral HPLC, and their absolute configurations for each pair of enantiomers have been determined by X-ray analysis. Individual enantiomers were screened in vitro for their antimycobacterial activities against Mycobacterium tuberculosis H37Rv, avium, terrae and extensively drug-resistant and multi-drug-resistant strains isolated from tuberculosis patients in Ural region (Russia). It has been shown that several compounds exhibit a good level of antituberculosis activity compared to the reference drugs. © ARKAT-USA, Inc.

Published
2014

41. Microwave-assisted palladium-catalyzed C-C coupling versus nucleophilic aromatic substitution of hydrogen (SN H) in 5-bromopyrimidine by action of bithiophene and its analogues

Author

Verbitskiy, E. V., Cheprakova, E. M., Zhilina, E. F., Kodess, M. I., Ezhikova, M. A., Pervova, M. G., Slepukhin, P. A., Subbotina, J. O., Schepochkin, A. V., Rusinov, G. L., Chupakhin, O. N., Charushin, V. N., Verbitskiy, E. V., Cheprakova, E. M., Zhilina, E. F., Kodess, M. I., Ezhikova, M. A., Pervova, M. G., Slepukhin, P. A., Subbotina, J. O., Schepochkin, A. V., Rusinov, G. L., Chupakhin, O. N., and Charushin, V. N.

Abstract

5-Bromopyrimidine reacts with 2,2′-bithiophene, [2,2′:5′, 2″]terthiophene and 2-phenylthiophene in the presence of a palladium catalyst to give 5-(het)aryl substituted pyrimidines due to the palladium-catalyzed aryl-aryl C-C coupling. However 5-bromo-4-(het)aryl- pyrimidines have been prepared from the same starting materials through the SN H-reaction catalyzed by a Lewis acid. Conditions for both types of reactions were optimized. All components of the reaction mixtures, including by-products, have been elucidated by gas-liquid chromatography/mass- spectrometry. Evidence for the structure of 4- and 5-bithiophenyl-substituted pyrimidines has first been obtained by means of X-ray crystallography analysis. Molecular orbital calculations (TDDFT), as well as the redox and optical measurements for all new compounds have also been performed. © 2013 Elsevier Ltd. All rights reserved.

Published
2013

46. Reactions of σH-adducts of 1-ethyl-1,4-diazinium salts with arylalkynes as a one-step approach to pyrrolo[1,2- a]pyrazine derivatives.

Author

Verbitskiy, E. V., Slepukhin, P. A., Ezhikova, M. A., Kodess, M. I., Rusinov, G. L., and Charushin, V. N.

Subjects
SALTS, PYRROLES, PYRAZINES, YLIDES, ACETYLENE
Abstract

The O- and C-adducts of 5-aryl and 5-hetaryl-2,3-dicyano-1-ethylpyrazinium salts are hidden sources of ylides, which can be used for the cyclization with arylacetylenes giving rise to pyrrolo[1,2- a]pyrazines. [ABSTRACT FROM AUTHOR]

Published
2009
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