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1.
Инвентарный номер: нет.
   
   T 19

   
    Tandem of nucleophilic substitution of hydrogen and cyclocondensation with participation of nitro group in the synthesis of fluorine-containing 3-amino-1,2,4-benzotriazines [Electronic resource] / G. A. Zhumabaeva, S. K. Kotovskaya, N. M. Perova, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 7. - P1243-1247
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Reactions of 3-fluoro-1-nitrobenzenes with guanidine hydrochloride in THF in the presence of ButOK gave isomeric 5-and 7-fluoro-containing 3-amino-1,2,4-benzotriazines

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (7), 1243.pdf
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2.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis, spectral and electrochemical properties of pyrimidine-containing dyes as photosensitizers for dye-sensitized solar cells [Electronic resource] / E. V. Verbitskiy [и др.] // Dyes and Pigments. - 2014. - Vol.100. - С. 201-214. - Bibliogr. : p. 213-214 (37 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ORGANIC DYES -- PYRIMIDINE -- MICROWAVE-ASSISTED
Аннотация: Six novel donor–π–acceptor organic dyes bearing a pyrimidine as the anchoring group have been obtained in good yields by combination of the microwave-assisted Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen reactions. Their absorption, photoluminescence and electrochemical properties were fully investigated in detail. The infrared spectra of dyes adsorbed on TiO2 indicate the formation of coordinate bonds between the pyrimidine ring of dyes and the Lewis acid sites (exposed Tin+ cations) of the TiO2 surface. This work demonstrates that the pyrimidine rings of dye sensitizers that form a coordinate bond with the Lewis acid site of a TiO2 surface are promising candidates as the electron-withdrawing anchoring group. The data from quantum calculations show that all of the dyes are potentially good photosensitizers for dye-sensitized solar cells

\\\\expert2\\NBO\\Dyes and Pigments\\2014, v. 100, p.201-214.pdf
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3.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis, Photophysical and Redox Properties of the D-pi-A Type Pyrimidine Dyes Bearing the 9-Phenyl-9H-Carbazole Moiety [Electronic resource] / E. V. Verbitskiy [и др.] // Journal of Fluorescence. - 2015. - Vol. 25, № 3. - С. 763-775. - Bibliogr. : p. 774-775 (51 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINES -- CARBAZOLE -- DYE-SENSITIZED SOLAR CELLS
Аннотация: Novel donor-pi-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in six aprotic solvents of various polarities have been studied by ultraviolet-visible and fluorescence spectroscopy. In contrast to the absorption spectra, fluorescence emission spectra displayed a strong dependence from their solvent polarities. The nature of the observed long wavelength maxima has been elucidated by means of quantum chemical calculations. The electrochemical properties of these dyes have been investigated by using cyclic voltammetry, while their photovoltaic performance was evaluated by a device fabrication study. The experimental and calculation data show that all of the dyes can be regarded as potentially good photosensitizers for dye-sensitized solar cells.

\\\\expert2\\nbo\\Journal of Fluorescence\\2015, v.25, p.763-775.pdf
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4.
Инвентарный номер: нет.
   

   
    Synthesis of meso-substituted calix[4]arenes via reaction of nucleophilic substitution of hydrogen (snh) in azine or azine-n-oxides / T. D. Moseev, M. V. Varaksin, I. A. Lavrinchenko [et al.] // Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - P273-274
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CALIX[4]ARENES -- AZINES -- C-C COUPLING -- NUCLEOPHILIC SUBSTITUTION OF HYDROGEN

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5.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of fluorine-containing quinoline-2,3-dicarboxylates from products of vicarious nucleophilic substitution of hydrogen in 3-fluoronitroarenes [Electronic resource] / S. K. Kotovskaya, G. A. Zhumabaeva, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 1. - P170-175
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reactions of 3-fluoro-4-R-6-phenylsulfonylmethylnitrobenzenes with dimethyl fumarate or diethyl maleate in acetonitrile in the presence of an excess of K2CO3 and a catalytic amount of 18-crown-6 afforded mixtures of dialkyl 6-R-7-fluoro- and dialkyl 6-R-7-phenylsulfonylquinoline-2,3-carboxylate N-oxides, as well as dialkyl 6-R-7-fiuoro- quinoline-2,3-carboxylates (alkyl is methyl or ethyl), which were resolved by column chromatography and identified by 1H NMR spectroscopy and X-ray diffraction

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (1), 170-175.pdf
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6.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of chiral ferrocenylazines. Negishi cross-coupling or S N H reactions? [Electronic resource] / A. A Musikhina, I. A. Utepova, N. S. Serebryakov, O. N. Chupakhin, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №8. - С. 1191-1194. - Bibliogr. : p. 1194 (28 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
SYNTHESIS -- CHIRAL FERROCENYLAZINES -- NEGISHI
Аннотация: Preparation of new hetaryl-containing planar chiral ferrocene by a nucleophilic substitution of hydrogen in azines was performed using a lithium derivative of (S)-ferrocenyl-p-tolylsulfoxide as s nucleophilic reagent

\\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (8), 1191-1194.pdf
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7.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of chelating polymer sorbents by using the S-N(H) methodology / A. V. Pestov, P. A. Slepukhin, Yu. G. Yatluk, V. N. Charushin, O. N. Chupakhin // Journal of Applied Polymer Science . - 2012. - Vol.125, №3. - С. 1970-1978
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
FUNCTIONALIZATION OF POLYMERS -- PHENOL -- X-RAY ANALYSIS
Аннотация: The article describes a new synthetic approach to modify the structure of phenol-formaldehyde and resorcinol-formaldehyde resins, which enables one to functionalize a polymer matrix by using the S?NH (nucleophilic aromatic substitution of hydrogen) methodology. Direct heteroarylation of phenol (resorcinol) fragments in polymer chains with 1,2,4-triazine derivatives illustrates a new synthetic method in the polymer chemistry. The feature of this methodology is that it provides an opportunity to accomplish direct one-pot polymer transformations by incorporating of rather complicated chelating groups through the displacement of hydrogen in phenol moieties. It has been shown that in order to obtain chemically modified polymers on the basis of phenol-formaldehyde and resorcinol-formaldehyde resins with a high degree of substitution with chelating units, a polymer matrix has to react with 3-(pyridin-2'-yl)-1,2,4-triazin-5(2H)-one. Also, it has been found that polymer sorbents with a high selectivity can be obtained by using the template method. Targeted synthesis of model compounds, as structural units of the chelating polymers, and elucidation of the structure of their complexes with copper (II) ions have shown that the most plausible type of coordination is formation of the bridge 1 : 1 complexes of the a,a'-bipyridinyl type.

\\\\expert2\\nbo\\Journal of Applied Polymer Science\\2012, vol.125,p.1970.pdf
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8.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis of 4-(thien-2-yl)-substituted coumarins through Lewis acid catalyzed Michael addition of thiophenes to 3-benzoylcoumarins followed by oxidation [Electronic resource] / R. A. Irgashev, A. A. Karmatsky, G. L. Rusinov, V. N. Charushin // Tetrahedron Letters. - 2014. - Vol.55, №26. - С. 3603-3606
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
THIOPHENES -- 3-BENZOYLCOUMARINS -- Lewis acid
Аннотация: 3-Benzoyl-4-(thien-2-yl)coumarins have been obtained in good yields according to the SNH addition–oxidation protocol, involving the diastereoselective addition of thiophenes at C-4 of 3-benzoylcoumarins under BBr3 catalysis, followed by oxidation of the intermediate 3,4-trans-3-benzoyl-4-(thien-2-yl)-3,4-dihydrocoumarins with DDQ. This two-step procedure can be regarded as nucleophilic substitution of hydrogen (SNH) on the heterocyclic ring of coumarins

\\\\expert2\\nbo\\Tetrahedron Letters\\2014, v. 55, p. 3603.pdf
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9.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and evaluation of antitubercular activity of fluorinated 5-aryl-4-(hetero)aryl substituted pyrimidines [Электронный ресурс] / E. V. Verbitskiy, S. A. Baskakova, M. A. Kravchenko, S. N. Skornyakov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Bioorganic and Medicinal Chemistry. - 2016. - Vol. 24, № 16. - С. 3771-3780
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINE -- ANTIMYCOBACTERIAL ACTIVITY -- TUBERCULOSIS
Аннотация: Various 5-(fluoroaryl)-4-(hetero)aryl substituted pyrimidines have been synthesized based on the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (S-N(H)) reactions starting from commercially available 5-bromopyrimidine and their antitubercular activity against Mycobacterium tuberculosis H(37)Rv has been explored. The outcome of the study disclose that, some of the compounds have showed promising activity in micromolar concentration against Mycobacterium tuberculosis H(37)Rv, Mycobacterium avium, Mycobacterium terrae, and multidrug-resistant strains isolated from tuberculosis patients in Ural region (Russia). The data concerning the 'structure-activity' relationship for fluorinated compounds have been discussed

\\\\expert2\\NBO\\Bioorganic and Medicinal Chemistry\\2016, V.24, N 16, p.3771-3780.pdf
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10.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and biological evaluation of novel 5-aryl-4-(5-nitrofuran-2-yl)-pyrimidines as potential anti-bacterial agents / E. V. Verbitskiy [et al.] // Bioorganic and Medicinal Chemistry Letters. - 2017. - Vol. 27, № 13. - P3003-3006
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINE -- NITROFURAN -- ANTIGONORRHEAL -- ANTIMYCOBACTERIAL -- NUCLEOPHILIC AROMATIC SUBSTITUTION OF HYDROGEN
Аннотация: A facile two-step synthetic approach to fluorinated and non-fluorinated 5-aryl-4-(5-nitrofuran-2-yl)-pyrimidines from readily available 5-bromo-4-(furan-2-yl)pyrimidine has been developed. All synthesized compounds were screened in vitro for their antibacterial activities against twelve various bacterial strains. It is demonstrated that some of these compounds exhibited significant antibacterial activities against strains Neisseria gonorrhoeae and Staphylococcus aureus, comparable and even higher with that commercial drug Spectinomycin.

\\\\Expert2\\NBO\\Bioorganic and Medicinal Chemistry Letters\\2017 v.27 p.3003-3006.pdf
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11.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions [Electronic resource] / M. A. Kravchenko, E. V. Verbitskiy, I. D. Medvinskiy, G. L. Rusinov, V. N. Charushin // Bioorganic and Medicinal Chemistry Letters. - 2014. - Vol. 24, №14. - С. 3118-3120
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINE -- ANTIMICOBACTERIAL -- TUBERCULOSIS
Аннотация: Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, avium, terrae, and multi-drug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs

\\\\expert2\\nbo\\Bioorganic and Medicinal Chemistry Letters\\2014, v. 24, p. 3118.pdf
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12.
Инвентарный номер: нет.
   
   S 90

   
    Study of the supramolecular structures of complexes of carborane-containing pyridazines with 2,3,5,6-tetrachloro-1,4-dihydroxybenzene [Electronic resource] / P. A. Slepukhin, S. G. Tolshchina, A. V. Ignatenko, E. F. Zhilina, V. N. Charushin // Crystallography Reports. - 2014. - Vol.59, №2. - С. 202-206. - Bibliogr. : p. 206 (9 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIDAZINES -- HETEROCYCLIC SUBSTITUENTS -- CARBORANE MOIETY
Аннотация: The structures and characteristic features of the molecular packing patterns of complexes of pyridazines containing heterocyclic substituents and the carborane moiety with 2,3,5,6-tetrachlorohydroquinone (TCHQ) were investigated. It was shown that TCHQ can form supramolecular assemblies with carborane-containing substituted pyridazines. The stoichiometry and three-dimensional structures of these assemblies depend on the substituents in the pyridazine ring and are formed via O-H⋯N hydrogen bonding between TCHQ and heterocyclic molecules

\\\\expert2\\NBO\\Crystallography Reports (Кристаллография)\\2014, v.59, N 2, p.202-206.pdf
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13.
Инвентарный номер: нет.
   
   S 90

   
    Study of the supramolecular structures of complexes of carborane-containing pyridazines with 2,3,5,6-tetrachloro-1,4-dihydroxybenzene [Electronic resource] / P. A. Slepukhin, S. G. Tolshchina, N. K. Ignatenko, R. I. Ishmetova, G. L. Rusinov, E. F. Zhilina, V. N. Charushin // Crystallography Reports. - 2014. - Vol. 59, № 2. - С. 202-206. - Bibliogr. : p. 206 (9 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
MOLECULAR PACKING PATTERNS -- PYRIDAZINES CONTAINING HETEROCYCLIC SUBSTITUENTS -- TETRACHLOROHYDROQUINONE
Аннотация: The structures and characteristic features of the molecular packing patterns of complexes of pyridazines containing heterocyclic substituents and the carborane moiety with 2,3,5,6-tetrachlorohydroquinone (TCHQ) were investigated. It was shown that TCHQ can form supramolecular assemblies with carborane-containing substituted pyridazines. The stoichiometry and three-dimensional structures of these assemblies depend on the substituents in the pyridazine ring and are formed via O-H…N hydrogen bonding between TCHQ and heterocyclic molecules

\\\\expert2\\nbo\\Crystallography Reports (Кристаллография)\\2014, v.59, N 2, p.202-206.pdf
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14.
Инвентарный номер: нет.
   
   C 57

    Chupakhin, O. N.
    Recent advances in the field of nucleophilic aromatic substitution of hydrogen [Electronic resource] / O. N. Chupakhin, V. N. Charushin // Tetrahedron Letters. - 2016. - Vol. 57, № 25. - С. 2665-2672
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
C-H FUNCTIONALIZATION -- S-N(H) METHODOLOGY -- OXIDATIVE ALKYLAMINATION
Аннотация: Recent advances in the filed of direct C-H functionalization of aromatics and heteroaromatics through nucleophilic displacement of hydrogen in an aromatic ring are discussed

\\\\expert2\\NBO\\Tetrahedron Letters\\2016, v. 57, p. 2665.pdf
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15.
Инвентарный номер: нет.
   
   P 17

   
    Palladium(II)-Catalyzed Oxidative C–H/C–H Coupling and Eliminative SNH Reactions in Direct Functionalization of Imidazole Oxides with Indoles / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Journal of Organic Chemistry. - 2012. - Vol.77, №20. - С. 9087-9093
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
IMIDAZOLE OXIDES -- INDOLES
Аннотация: Two novel synthetic approaches to realize the direct C(sp2)–H bond functionalization in cyclic nitrones are reported. Palladium(II)-catalyzed oxidative C–C coupling of 2,2-dialkyl-4-phenyl-2H-imidazole 1-oxides with indoles was shown to result in the formation of 5-indolyl-3-yl derivatives, while nucleophilic substitution of hydrogen (SNH) at C(5) of the same imidazole system was found to afford the corresponding deoxygenated compounds

\\\\Expert2\\nbo\\Journal of Organic Chemistry\\2010, v.77, p.9087.pdf
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16.
Инвентарный номер: нет.
   
   O-72

   
    Organolithium compounds in the nucleophilic substitution of hydrogen in arenes and hetarenes [Electronic resource] / I. S. Kovalev, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Russian Chemical Reviews. - 2015. - Vol. 84, № 12. - С. 1191-1225. - Bibliogr. : p. 1224-1225 (237 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
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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17.
Инвентарный номер: нет.
   
   C 57

    Chupakhin, O. N.
    Nucleophilic substitution of hydrogen in azines [Electronic resource] / O. N. Chupakhin, V. N. Charushin, H. C. Van der Plas // Tetrahedron. - 1988. - Vol. 44, № 1. - С. 1-34. - Bibliogr. : p. 32-34 (186 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
AZINES -- HYDROGEN

\\\\expert2\\nbo\\Tetrahedron\\1988, v. 44, p. 1-34.pdf
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18.
Инвентарный номер: нет.
   
   C 47

    Charushin, V. N.
    Nucleophilic aromatic substitution of hydrogen and related reactions [Electronic resource] / V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2007. - Vol. 17, № 5. - P249-254
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The classical concept of nucleophilic aromatic substitution (SNAripso) has been complemented with a new synthetic methodology (SNH), enabling one to build new carbon–carbon C(sp2)–C(sp3), C(sp2)–C(sp2) and C(sp2)–C(sp) or carbon–heteroatom C(sp2)–X (X is O, N, P, S, halogen) bonds through nucleophilic displacement of hydrogen in an aromatic ring.

\\\\Expert2\\nbo\\Mendeleev Communications\\2007, v.17, p.249.pdf
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19.
Инвентарный номер: нет.
   
   C 57

    Chupakhin, O. N.
    Nucleophilic aromatic substitution of hydrogen [Text] : научное издание / O. N. Chupakhin, V. N. Charushin, Henk C. van der Plas. - [S. l.] : Academic Press, 1994. - 376p. - Б. ц.
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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20.
Инвентарный номер: нет.
   

   
    Novel pentafluorophenyl- and alkoxyphenyl-appended 2,2'-bipyridine push-pull fluorophores: a convenient synthesis and photophysical studies / T. D. Moseev, E. A. Nikiforov, M. V. Varaksin [et al.] // Synthesis. - 2021. - Vol. 53, № 19. - P3597-3607
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
2,2′-BIPYRIDINES -- 1,2,4-TRIAZINES -- POLYFLUOROARENES
Аннотация: A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2′-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (SN H) in 1,2,4-triazine precursors via the ‘addition–elimination’ scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2′-bipyridines by means of the aza-Diels–Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2′-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push–pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert–Mataga equation.

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