Synthesis of new polycyclic systems based on [1,2,5]chalcogenodiazolo[3,4-b]thieno[3,2-h]quinoxalines

Article Chemistry, Multidisciplinary

First synthesis of new polycyclic systems from ortho-di(heteroaryl)-substituted furazanopyrazine derivatives by the Scholl reaction

Egor V. Verbitskiy et al.

Summary: A facile synthetic protocol for the synthesis of hard-to-get polycyclic (hetero)-aromatic compounds annulated to [1,2,5]oxadiazolo[3,4-b]-pyrazine scaffold via FeCl3-mediated intramolecular Scholl cross-coupling has been developed. The synthesized polycyclic systems exhibit narrow band gaps (ranging from 1.42 to 1.89 eV) and can be considered as n-type organic semiconductors with energy levels comparable to commercially available n-type semiconductors.

MENDELEEV COMMUNICATIONS (2022)

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Article Biochemistry & Molecular Biology

Push-Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-B]Pyrazine and [1,2,5]Thiadiazolo[3,4-B]Pyrazine Electron Withdrawing Parts

Egor V. Verbitskiy et al.

Summary: In this study, a series of novel V-shaped derivatives were designed and investigated for their electrochemical, photophysical and nonlinear optical properties. The [1,2,5]oxadiazolo[3,4-b]pyrazine fragment was found to be a strong electron-withdrawing group. All compounds exhibited emissions in the solid state, while only the quinoxaline derivatives emitted in a DCM solution. The quinoxaline derivatives demonstrated solvatochromism and extra-large Stokes shifts, indicating twisted intramolecular charge transfer excited states and aggregation induced emission.

MOLECULES (2022)

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Review Chemistry, Multidisciplinary

Modification and application of 1,2,5-oxadiazolo[3,4-b]pyrazine derivatives: highlights and perspectives

Yu A. Kvashnin et al.

Summary: This review summarized and classified the data on the construction of [1,2,5]oxadiazolo[3,4-b]pyrazine scaffold and its further modifications published over the past 20 years, with a special consideration given to synthetic approaches based on the reactions of the direct C-H bond functionalization. Promising practical applications of furazanopyrazines are also provided.

RUSSIAN CHEMICAL BULLETIN (2022)

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Article Chemistry, Multidisciplinary

Structures of reaction products of 5,6-dichlorofurazano[3,4-b]pyrazine with R-hydrazines

S. E. Tolstikov et al.

Summary: The reaction of 5,6-dichlorofurazano[3,4-b]pyrazine with phenyl- and methylhydrazines was investigated to synthesize furazano[3,4-b]pyrazine derivatives that can potentially be oxidized to paramagnetic derivatives. New polyheterocyclic compounds containing the furazano[3,4-b]pyrazine structural moiety annulated to the tetrazine or triazole ring were successfully synthesized. The structures of all compounds were confirmed by X-ray diffraction.

RUSSIAN CHEMICAL BULLETIN (2022)

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Article Chemistry, Physical

Synthesis, photophysical and nonlinear optical properties of [1,2,5] oxadiazolo[3,4-b]pyrazine-based linear push-pull systems

Egor V. Verbitskiy et al.

Summary: A series of D-pi-A chromophores based on [1,2,5]oxadiazolo[3,4-b]pyrazine electron-withdrawing group were designed and studied using cyclic voltammetry, UV-Vis, emission spectroscopy, and EFISH method. The influence of pi-conjugated linkers and amino-electron-donating groups on the properties of the chromophores were analyzed experimentally and theoretically, including their second order nonlinear optical properties.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Novel organic magnet derived from pyrazine-fused furazans

Victor I. Ovcharenko et al.

Summary: The first organic magnet based on a high-nitrogen framework of pyrazine-fused furazans Na(L center dot-)(H2O)(3) was discovered. A quantum-chemical study of M(L center dot-)(H2O)(n) showed that the exchange coupling energy between neighboring radical anions is highly sensitive to the motion of one L center dot- relative to another.

MENDELEEV COMMUNICATIONS (2021)

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Review Chemistry, Multidisciplinary

Chalcogen exchange in chalcogen-nitrogen π-heterocycles

Lidia S. Konstantinova et al.

Summary: This review discusses the procedures, scope, and reaction pathways for synthesizing fused 1,2,5-chalcogenadiazoles and 1,2,3-dithiazoles by direct exchange of one chalcogen atom for another.

MENDELEEV COMMUNICATIONS (2021)

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Review Chemistry, Multidisciplinary