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Тематика научных публикаций
Mikhail Yu. Belikov, Mikhail Yu. Ievlev, Sergey V. Fedoseev
and Oleg V. Ershov
New J. Chem., 2019,43, 8414-8417
Tuning the photochromic properties of chromophores containing a nitrile-rich acceptor: a novel branch in the investigation of negative photochromes
Various negative photochromes containing a nitrile-rich acceptor with tunable absorption properties and thermal stability of the photo-induced form were synthesized and characterized. High photoswitching contrast due to the contribution of an intensely colored quinoid form of the chromophores of this series was shown for the first time. The obtained results discovered a new direction in the investigation of negative photochromes.
Sergey V.Fedoseev, Mikhail Yu.Belikov, Mikhail Yu.Ievlev, Oleg V. Ershov, and Viktor A.Tafeenko
Dyes and Pigments, 2019, 165, 451-457
Tuning solid-state fluorescence of a novel group D-π-A chromophores with a reactive hydroxytricyanopyrrole (HTCP) acceptor
The approach to novel group of donor-acceptor chromophores exhibiting solid-state fluorescence based on the reaction of hydroxytricyanopyrrole (HTCP) acceptor with methoxybenzaldehydes has been developed. The presence of a hydroxyl group in the structure of synthesized chromophores allows functionalizing them and tuning their fluorescent properties, varying maxima of emission in a range of 518–617 nm. The developed method is of interest as it is a promising approach to a new group of fluorescent push-pull D-π-A chromophores, which are functionalized analogues of known chromophores based on the tricyanofuran (TCF) acceptor.
Vladimir Р. Sheverdov, Vera V. Davydova,Oleg E. Nasakin, Maksim A. Mar’yasov, Olga A. Lodochnikova
Synlett, 2019, 30(02), 173-177
Ethene-1,1,2,2-tetracarbonitrile and Methanol in the Methylating Reaction of Tertiary Amines to the Quaternary Ammonium Compounds of 1,1-Dicyano-2-methoxy-2-oxoethane-1-ide
We discovered a new method to methylate tertiary amines such as urotropine, triethylamine, pyridine, 2-methylpyridine, 4-acetylpyridine, and isonicotinamide, up to quaternary ammonium compounds, with 1,1-dicyano-2-methoxy-2-oxoethane-1-ide being the counterion. Quaternary ammonium compounds of 1,1-dicyano-2-methoxy-2-oxothane-1-ide were synthesized within a single stage by stirring methanol solutions of tertiary amines with ethene-1,1,2,2-tetracarbonitrile (ETCN) at room temperature. In the reaction of ETCN with tertiary amines in methanol, processes occur that form the 1,1-dicyano-2-methoxy-2-oxoethane-1-ide fragment with simultaneous N-methylation. Crystal structures based on X-ray diffraction analysis of the obtained compounds were studied. .
Sergey S. Chunikhin, Oleg V. Ershov, Mikhail Yu. Ievlev, Mikhail Yu. Belikov and Viktor A. Tafeenko
Dyes and Pigments, 2018, 156, 357-368
Novel chromophores of cyanopyridine series with strong solvatochromism and near-infrared solid-state fluorescence
A series of novel pyridine derivatives containing tetracyanobutadiene moiety (4-CN-TCPy) were obtained in good yields by the reaction of 2-chlorosubstituted pyridine-3,4-dicarbonitriles with malononitrile using Cs2CO3 as a catalyst. The resulting 4-CN-TCPy are stable intensively colored substances possessing a solid-state emission in the red and near-infrared region. Solutions thereof are characterized with a strong solvatochromic effect as well as weak blue fluorescence.
Ya. S. Kayukov, S. V. Karpov, A. A. Grigor'ev, O. E. Nasakin, V. A. Tafeenko, K. A. Lyssenko, A. V. Shapovalov and E. A. Varaksina
Dalton Transactions, 2017, 46, 16925-16938
2-Acyl-1,1,3,3-tetracyanopropenides (ATCN): structure characterization and luminescence properties of ammonia and alkali metal ATCN salts
Herein, syntheses, crystal structures, and photoluminescence properties of 24 new ammonia and alkali metal ATCN salts characterized via single-crystal X-ray diffraction are reported. It was estimated that most ATCN powders exhibited yellow-green fluorescence (at 450–600 nm). For samples that possess fluorescence of low intensity in the solid state, several optical centers of emission exist. ATCN being a new representative of stable tetracyanoallyl salts is a promising candidate for creation of various 1D, 2D, and 3D supramolecular structures and potential functional materials
O. V. Ershov, M. Yu. Ievlev, M. Yu. Belikov, A. I. Naidenova,
V. N. Maksimova and V. A. Tafeenko
RSC Advances, 2017, 7, 34886-34891
Synthesis, solution and solid-state fluorescence of 2-diethylaminocinchomeronic dinitrile derivatives
A facile approach to the synthesis of novel 2-diethylaminocinchomeronic dinitriles, which are found to be fluorescent both in the solution and in a solid states, was developed. Absorption, fluorescence and solvatochromic properties as well as a crystal structure of the synthesized compounds were investigated. It was found that the 2-diethylaminocinchomeronic dinitrile derivatives with methoxy groups in the aryl moiety possess the most intensive emission in nonpolar solvents with fluorescence quantum yields up to 0.59.
Sergey V. Karpov, Arthur A. Grigor’ev, Yakov S. Kayukov, Irina V. Karpova, Oleg E. Nasakin, and Victor A. Tafeenko
J. Org. Chem., 2016, 81 (15), 6402–6408
Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO–NaBr–H2SO4 oxidation system. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of “green chemistry”. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry.
Oleg V. Ershov, Sergey V. Fedoseev, Mikhail Yu. Ievlev, Mikhail Yu. Belikov
Dyes and Pigments, 2016, 134, 459-464
2-Pyridone-based fluorophores: Synthesis and fluorescent properties of pyrrolo[3,4-c]pyridine derivatives
Several novel pyrrolo[3,4-c]pyridine derivatives were synthesized in good yields via hydrolysis and intramolecular heterocyclization of vicinal substituents in compounds of pyrid-2-one series. Both synthesized pyrrolo[3,4-c]pyridine-1,3,4-triones and 1-iminopyrrolo[3,4-c]pyridine-3,4-diones are fluorescent in various solvents with emission maxima in the blue-green region of the spectrum.
Mikhail Yu. Ievlev, Oleg V. Ershov, and Viktor A. Tafeenko
Organic Letters, 2016, 18 (8), 1940–1943
Diastereoselective Cascade Assembly of Functionalized Pyrano[3,4-c]pyrrole Derivatives
A novel convenient approach for the synthesis of densely functionalized pyrano[3,4-c]pyrrole derivatives was developed. Cascade transformation of the simple adducts of tetracyanoethylene (TCNE) and ketones (4-oxoalkane-1,1,2,2-tetracarbonitriles) in the presence of aldehyde under the action of acetic acid led to the diastereoselective formation of targeted pyrano[3,4-c]pyrroles. The reaction pathway was thoroughly investigated, and proposed intermediates were shown to be consistent with experiment.
Oleg V. Ershov, Mikhail Yu. Ievlev, V. A. Tafeenko and O. E. Nasakin
Green Chem., 2015,17, 4234-4238
Glycine catalyzed diastereoselective domino-synthesis of 6-imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles in water
The first example of glycine-catalyzed direct domino synthesis of 6-imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles in aqueous medium is described, giving products in excellent yields and moderate to excellent diastereoselectivities. This approach provides a highly efficient and environmentally benign access to cyano-substituted 2,7-dioxabicyclo[3.2.1]octane.
Oleg V. Ershov, Sergey V. Fedoseev, Mikhail Yu. Belikov and
Mikhail Yu. Ievlev
RSC Advances, 2015, 5, 34191-34198
Domino-synthesis and fluorescence properties of 4-cyano-2-oxo-1,2-dihydropyridine-3-carboxamides and 2-oxo-1,2-dihydropyridine-3,4-dicarbonitriles
Non-catalytic conversion of 4-oxoalkane-1,1,2,2-tetracarbonitriles in the presence of water leads to the formation of a mixture of fluorescent 4-cyano-2-oxo-1,2-dihydropyridine-3-carboxamides and 2-oxo-1,2-dihydropyridine-3,4-dicarbonitriles in equal proportions. This transformation was explained, spectral-luminescence properties were investigated, and fluorescence quantum yield was measured..