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1.
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    (A)symmetric chromophores based on cyano and fluorine-substituted 2,3-bis(5-arylthiophen-2-yl)quinoxalines: Synthesis, photophysical properties and application prospects / T. N. Moshkina, E. V. Nosova, A. E. Kopotilova [et al.] // Dyes and Pigments. - 2022. - Vol. 204. - Ст. 110434
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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2.
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    1,2,4,5-Tetrazine derivatives as components and precursors of photo- and electroactive materials / G. N. Lipunova, E. V. Nosova, G. V. Zyryanov [et al.] // Organic chemistry frontiers. - 2021. - Vol. 8, № 18. - P5182-5205
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Extensive research on the synthesis and application of tetrazine derivatives for electronic devices, luminescent elements, photoelectric conversion elements, and image sensors has been published recently. This review covers reported data on the modern trends in the design of functionalized tetrazines obtained within the period 2010–2020. Aryl(heteroaryl) and arylvinyl derivatives of tetrazines and their photoluminescence and application for fluorogenic probes are discussed. Examples of photosensitive oligomers and polymer 3,6-dithienyltetrazines are reviewed.

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3.
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    1,3,7-triazapyrene-based ortho-carborane fluorophores: convenient synthesis, theoretical studies, and aggregation-induced emission properties / L. A. Smyshliaeva, M. V. Varaksin, E. I. Fomina [et al.] // Organometallics. - 2021. - Vol. 40, № 16. - P2792-2807
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SNH), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SNH transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects.

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4.
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    15N chemical shifts and Jnn-couplings as diagnostic tools for determination of the azide-tetrazole equilibrium in tetrazoloazines / S. L. Deev, T. S. Shestakova, Z. O. Shenkarev [et al.] // Journal of Organic Chemistry. - 2022. - Vol. 87, № 1. - P211–222
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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5.
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    2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines / A. P. Krinochkin, G. Mallikarjuna Reddy, D. S. Kopchuk [et al.] // Mendeleev Communications. - 2021. - Vol. 31, № 4. - P542-544
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1,2,4-TRIAZINES -- OXAZOL-2-AMINES -- DIELS–ALDER REACTION -- 2,2'-BIPYRIDIN-3-OLS
Аннотация: High temperature coupling of 6-aryl-5-cyano-3-(pyridin-2-yl)-1,2,4-triazines with 2-amino-4-aryloxazoles proceeds as the inverse demand Diels–Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene to construct new 4,5-diaryl-6-cyano-3-hydroxypyridin-2-yl fragment. A reaction mechanism is proposed, and the structure of the key-product is proved by the X-ray diffraction analysis.

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6.
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    9-substituted acridine derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors possessing antioxidant activity for alzheimer's disease treatment / G. F. Makhaeva [et al.] // Bioorganic and Medicinal Chemistry. - 2017. - Vol. 25, № 21. - P5981-5994
ББК 24
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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7.
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    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 / I. A. Lavrinchenko, T. D. Moseev, M. V. Varaksin [et al.] // New Journal of Chemistry. - 2022. - Vol. 46, № 11. - P5121-5128
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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8.
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   A 10


   
    A new approach to 4-arylstyrenes: microwave-assisted synthesis and photophysical properties / M. Z. Eddin, M. G. Pervova, E. F. Zhilina [et al.] // Russian chemical bulletin. - 2021. - Vol. 70, № 11. - P2139-2144
ББК Г
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
STYRENE -- 4-VINYLBIPHENYL DERIVATIVES -- SUZUKi—MIYAURA CROSS-COUPLING -- FLUORESCENCE

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9.
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    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 / O. S. Taniya, V. V. Fedotov, L. K. Sadieva [et al.] // Dyes and Pigments. - 2022. - Vol. 204. - Ст. 110405
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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10.
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    An efficient synthesis of push-pull fluorophores based on (2-fluoroaryl)-1,2,3-triazoles / I. A. Lavrinchenko, T. D. Moseev, Y. A. Seleznev [et al.] // Успехи синтеза и комплексообразования = Advances in synthesis and complexing : сборник тезисов шестой Международной научной конференции. - Москва, 2022. - P194
Рубрики: ХИМИЧЕСКИЕ НАУКИ

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