Ключевые научные работы сотрудников факультета, индексируемые системой Web of Science

 

Novel chromophores of cyanopyridine series with strong solvatochromism and near-infrared solid-state fluorescence

Abstract
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.

Sergey S. Chunikhin, Oleg V. Ershov, Mikhail Yu Ievlev,
Mikhail Yu Belikov and Viktor A. Tafeenko


Dyes and Pigments, 2018, 156, 357-368
DOI:10.1016/j.dyepig.2018.04.024

 

Dibromomalononitrile-potassium bromide complex as a mild bromination and oxidation reagent for the synthesis of mono-, di- and trimethoxyphenyl bromopyridines
 

Abstract
The synthesis of mono-, di- and trimethoxyphenyl bromopyridines using the dibromomalononitrile-potassium bromide complex as a mild bromination and oxidation reagent is described.

 

 

Ivan N. Bardasov, Anastasiya U. Alekseeva, Oleg V. Ershov


Tetrahedron Letters, 2018, 59 (14), 1398-1399

DOI: 10.1016/j.tetlet.2018.02.069

 

2-Acyl-1,1,3,3-tetracyanopropenides (ATCN): structure characterization and luminescence properties of ammonia and alkali metal ATCN salts

Abstract
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

 

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 
DOI:10.1039/C7DT03625F

 

Synthesis, solution and solid-state fluorescence of 2-diethylaminocinchomeronic dinitrile derivatives
 

Abstract
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.

 

 

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
DOI: 10.1039/C7RA06217F 

 

Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides
 

Abstract
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.

 

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
DOI: 10.1021/acs.joc.6b01040

 

2-Pyridone-based fluorophores: Synthesis and fluorescent properties of pyrrolo[3,4-c]pyridine derivatives

Abstract
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.

 

Oleg V. Ershov, Sergey V. Fedoseev, Mikhail Yu. Ievlev, Mikhail Yu. Belikov



Dyes and Pigments, 2016, 134, 459-464
DOI: 10.1016/j.dyepig.2016.07.037

 

Diastereoselective Cascade Assembly of Functionalized Pyrano[3,4-c]pyrrole Derivatives

Abstract
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.

Mikhail Yu. Ievlev, Oleg V. Ershov, and Viktor A. Tafeenko

 

 


Organic Letters, 2016, 18 (8), 1940–1943
DOI: 10.1021/acs.orglett.6b00867

 

 

Glycine catalyzed diastereoselective domino-synthesis of 6-imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles in water

Abstract
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,  Mikhail Yu. Ievlev, V. A. Tafeenko  and  O. E. Nasakin

Green Chem., 2015,17, 4234-4238 
DOI: 10.1039/C5GC00909J

   
   
   

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