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1.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Lavrinchenko I. A., Moseev T. D., Varaksin M. V., Zyryanov G. V., Taniya O. S., Tsmokalyuk A. N., Charushin V. N., Chupakhin O. N., Demidov O. P., Borovlev I. V.
Заглавие : A BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in the design of push–pull fluorophores and chemosensors for nitroaromatics
Место публикации : New Journal of Chemistry. - 2022. - Vol. 46, № 11. - С. 5121-5128
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Mono- and bis-2-thienyl-substituted 1,3,7-triazapyrenes have been synthesized for the first time via BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in 33 and 51% yields, respectively. The photophysical properties of these polycyclic azaaromatics have been studied, with emission in the range of 450–500 nm and fluorescence quantum yields of up to 99% in methanol solutions being revealed. The turn-off chemosensing properties of 2-thienyl-substituted 1,3,7-triazapyrenes for the selective detection of nitroaromatics have also been assessed; in particular, the quenching constants according to the Stern–Volmer model, the quenching sphere radius according to the Perrin model, the detection limit and the quenching efficiency have been determined. In particular, 6,8-bis-(thiopen-2-yl)-1,3,7-triazapyrene, characterized by 10 times the quenching constant and limit of detection (LOD) compared to the mono-substituted analog, can be considered as the most promising chemosensor for determining nitroaromatic compounds. DFT calculations confirm the presence of intramolecular charge transfer (ICT) effects in the case of the obtained fluorophores and clarify the quenching mechanism for nitroaromatics.
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2.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Deev S. L., Shestakova T. S., Shenkarev Z. O., Paramonov A. S., Khalymbadzha I. A., Eltsov O. S., Charushin V. N., Chupakhin O. N.
Заглавие : 15N chemical shifts and Jnn-couplings as diagnostic tools for determination of the azide-tetrazole equilibrium in tetrazoloazines
Место публикации : Journal of Organic Chemistry. - 2022. - Vol. 87, № 1. - С. 211–222
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Selectively 15N-labeled tetrazolo[1,5-b][1,2,4]triazines and tetrazolo[1,5-a]pyrimidines bearing one, two, or three 15N labels were synthesized. The synthesized compounds were studied by 1H, 13C, and 15N NMR spectroscopy in DMSO and TFA solutions, where the azide–tetrazole equilibrium can lead to the formation of two tetrazole (T, T′) isomers and one azide (A) isomer for each compound. Incorporation of the 15N-label(s) leads to the appearance of 15N–15N coupling constants (JNN), which can be easily measured via simple 1D 15N NMR spectra, even at natural abundance between labeled and unlabeled 15N atoms. The chemical shifts for the 15N nuclei in the azole moiety are very sensitive to the ring opening and azide formation, thus providing information about the azido–tetrazole equilibrium. At the same time, the 1–2JNN couplings between 15N-labeled atoms in the azole and azine fragments unambiguously determine the fusion type between tetrazole and azine rings in the cyclic isomers T and T′. Thus, combined analysis of 15N chemical shifts and JNN values in selectively isotope-enriched compounds provides an effective diagnostic tool for direct structural determination of tetrazole isomers and azide form in solution. This method was found to be the most simple and efficient way to study the azido–tetrazole equilibrium.
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3.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Korotina A. V., Tolshchina S. G., Ishmetova R. I., Rusinov G. L., Chupakhin O. N., Charushin V. N., Evstigneeva N. P., Gerasimova N. A., Zil’berberg N. V., Kungurov N. V.
Заглавие : Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity
Место публикации : Beilstein Journal of Organic Chemistry. - 2022. - Vol. 18. - С. 243-250
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A series of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines has been synthesized through oxidation reaction of the corresponding 3,6-disubstituted 1,2,4,5-tetrazines bearing amidine fragments. It is shown that the heterocyclic systems obtained can be modified easily at C(3) position in the reactions with aliphatic alcohols and amines. Also, the reactivity of [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines towards CH-active compounds has been studied. The obtained triazolo[1,5-b]annulated 1,2,4,5-tetrazines proved to be active in micromolar concentrations in vitro against filamentous anthropophilic and zooanthropophilic dermatophyte fungi (Trichophyton, Microsporum and Epidermofiton), which cause skin and its appendages (hair, nails) diseases.
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4.

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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5.

Вид документа : Статья из журнала
Шифр издания : Г/B 68
Автор(ы) : Akulov A. A., Varaksin M. V., Tsmokalyuk A. N., Charushin V. N., Chupakhin O. N.
Заглавие : Blue-light-promoted radical c-h azolation of cyclic nitrones enabled by selectfluor®
Место публикации : Green Chemistry. - 2021. - Vol. 23, № 5. - С. 2049-2057
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: An original approach to achieve the C(sp2)–H azolation of cyclic aldonitrones mediated by Selectfluor® has first been employed. By exploiting a metal-free, visible-light-promoted cross-dehydrogenative C–N coupling reaction between model aldonitrones, 2H-imidazole 1-oxides, and NH-containing azoles, a series of novel azaheterocyclic derivatives have been obtained in yields up to 94%. The elaborated protocol has proved to be appropriate for gram-scale processes and displayed potential for utilization in the synthesis of novel structural analogues of lanabecestat. Besides, mechanistic studies have revealed that this coupling reaction is likely to proceed via a nitroxide-involving radical pathway, encompassing a chain of electron transfer events, such as hydrogen atom transfer (HAT) and single electron transfer (SET).
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6.

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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7.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Moshkina T. N., Nosova E. V., Charushin V. N., Lipunova G. N., Valova M. S., Petrusevich E. F., Zalesny R., Osmialowski B.
Заглавие : Substituted 2-(2-hydroxyphenyl)–3H-quinazolin-4-ones and their difluoroboron complexes: Synthesis and photophysical properties
Место публикации : Spectrochimica acta part A: molecular and biomolecular spectroscopy. - 2021. - Vol. 252. - С. 119497
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): esipt--fluorescence--o-ligand--bf2-complex2-(2-hydroxyphenyl)–3h-quinazolin-4-ones
Аннотация: 2-(2-Hydroxyphenyl)–3H-quinazolin-4-ones with diverse substituents at phenol ring and their six-membered difluoroboron complexes have been synthesized via few-stage approach. The photophysical properties of target compounds have been investigated in two solvents as well as in the solid state. The nature of substituents and substitution point in the phenol moiety of ligands and resulting BF2-complexes on the photophysical properties of dyes have been explored. The complex bearing two t-Bu groups proved to be the most emissive in solid state, whereas its 5-methoxy and 4-diethylamino counterparts possess strong emission in toluene solution. The dyes exhibited large Stokes shifts which was attributed to excited state intramolecular proton transfer (ESIPT). Additionally, fluorescence of quinazolinones in the mixture of THF/water was studied. All ligands demonstrated emission enhancement with increase of water fraction which was due to aggregation induced emission.
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8.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Deev S. L., Sheina E., Shestakova T. S., Khalimbadzha I., Charushin V. N., Chupakhin O. N., Batsyts S., Namyslo J. C., Schmidt A., Kiskin M. A., Paramonov A. S., Shenkarev Z. O.
Заглавие : Betaine–N-heterocyclic carbene interconversions of quinazolin-4-one imidazolium mesomeric betaines. sulfur, selenium, and borane adduct formation
Место публикации : European journal of organic chemistry. - 2020. - № 4. - С. 450-465
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): anionic nhcs--betaines--boron compounds--carbenes--cyclic borates--imidazol-2-ylidene
Аннотация: Reaction of N-alkylated imidazoles with 2-chloro-4-quinazolinone gave mesomeric betaines, 2-(1-alkyl-1H-imidazolium-3-yl)quinazolin-4-olates, for which three tautomeric forms of N-heterocyclic carbenes (NHCs) can be formulated, in addition to an anionic NHC after deprotonation. The NHC tautomers were trapped with sulfur, selenium, triethylborane, and triphenylborane as thiones, selenones and borane adducts, respectively. We obtained two isomers of the cyclic borane adducts, diazaboroloquinazolinones with [1,5-a] and [5,1-b]-type fusion between the quinazolinone and the diazaborole rings. They correspond to two different NHC tautomers and to the anionic NHC derived thereof. The third NHC tautomer was trapped as a non-cyclic adduct with tris(pentafluorophenyl)borane by coordination to the quinazoline oxygen atom. 2D 1H-15N HMBC experiments of 15N-labeled quinazolinone fragments, quantitative measurements of long-range 1H-15N coupling constants (JHN), and five X-ray single crystal analyses have been carried out for the structure elucidations and to gain insight into the NMR spectroscopic properties of these compounds.
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9.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Verbitskiy E. V., Kvashnin Y. A., Zhilina E. F., Shchepochkin A. V., Rusinov G. L., Chupakhin O. N., Charushin V. N., Baranova A. A., Khokhlov K. O., Chuvashov R. D., Schapov I. E., Yakovleva Y. A., Makarova N. I., Vetrova E. V., Metelitsa A. V.
Заглавие : Synthesis and characterization of linear 1,4-diazine-triphenylamine–based selective chemosensors for recognition of nitroaromatic compounds and aliphatic amines
Место публикации : Dyes and pigments. - 2020. - Vol. 178. - С. 108344
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): aliphatic amines--fluorescence quenching--nitroaromatic compounds--pyrazine--quinoxaline--solvatochromism
Аннотация: Novel 1,4-diazine-based dyes of the D–π–A type, possessing triphenylamine as an electron-donating group, have been developed. Fluorescence studies have demonstrated that emission of these fluorophores is sensitive towards different nitroaromatic compounds and aliphatic amines, both in solutions and in a vapor phase. Moreover, these compounds can be considered as “naked-eye” fluorescent probes for solution polarity because they possess pronounced solvatochromic properties. Therefore, these compounds have to be regarded as potential multifunctional chemosensors for monitoring hazardous organic substances.
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10.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Smyshliaeva L. A., Varaksin M. V., Charushin V. N., Chupakhin O. N.
Заглавие : Azaheterocyclic derivatives of ortho -carborane: synthetic strategies and application opportunities
Место публикации : Synthesis. - 2020. - Т. 52, № 3. - С. 337-352
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): carboranes--azaheterocycles--decaborane--cross-coupling reactions--carboryne
Аннотация: Azaheterocyclic derivatives of 1,2-dicarba- closo -dodeca borane (ortho -carborane) are known to be of particular interest due to numerous plausible applications, particularly, in medicine, materials science, and advanced technologies. Three principal synthetic strategies resulting in azaheterocyclic carboranes, in which boron-enriched and azaheterocyclic fragments are linked to each other, either directly by means of the C-C bonds or through a short spacer (CH 2, CH 2 S, CH 2 O, etc.), have been outlined. These synthetic approaches are of general character and can be used both individually and in combination to afford promising organoboron clusters of diverse architectures. 1 Introduction 2 C-C Cross-Coupling Strategies in the Synthesis of Azahetero cyclic Carboranes 3 Carboryne-Based Transformation Strategies 4 Condensation Strategies: Reactions of Decaborane B 10 H 14 with Substituted Acetylenes 5 Conclusion and Outlook.
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