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Article

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

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I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620108 Ekaterinburg, Russia
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Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, Mira St. 19, 620002 Ekaterinburg, Russia
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University Rennes, CNRS, Institut des Sciences Chimiques de Rennes—UMR 6226, 35000 Rennes, France
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Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice Studenská 573, 53210 Pardubice, Czech Republic
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Département d’Optique Ultrarapide et Nanophotonique, IPCMS, UMR CNRS 7504, Université de Strasbourg, 23 rue du Loess, BP 43, CEDEX 2, 67034 Strasbourg, France
*
Authors to whom correspondence should be addressed.
Academic Editor: Fernando Baiao Dias
Molecules 2022, 27(13), 4250; https://doi.org/10.3390/molecules27134250
Received: 11 June 2022 / Revised: 28 June 2022 / Accepted: 29 June 2022 / Published: 30 June 2022
(This article belongs to the Special Issue Novel Fluorophores and Their Applications)
A series of novel V-shaped quinoxaline, [1,2,5]oxadiazolo[3,4-b]pyrazine and [1,2,5]thiadiazolo[3,4-b]pyrazine push–pull derivatives with 2,4′-biphenylene linker were designed and their electrochemical, photophysical and nonlinear optical properties were investigated. [1,2,5]Oxadiazolo[3,4-b]pyrazine is the stronger electron-withdrawing fragment as shown by electrochemical, and photophysical data. All compounds are emissive in a solid-state (from the cyan to red region of the spectrum) and quinoxaline derivatives are emissions in DCM solution. It has been found that quinoxaline derivatives demonstrate important solvatochromism and extra-large Stokes shifts, characteristic of twisted intramolecular charge transfer excited state as well as aggregation induced emission. The experimental conclusions have been justified by theoretical (TD-)DFT calculations. View Full-Text
Keywords: furazanopyrazine; [1,2,5]thiadiazolo[3,4-b]pyrazine; quinoxaline; donor–acceptor systems; twisted intramolecular charge transfer furazanopyrazine; [1,2,5]thiadiazolo[3,4-b]pyrazine; quinoxaline; donor–acceptor systems; twisted intramolecular charge transfer
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MDPI and ACS Style

Verbitskiy, E.V.; le Poul, P.; Bureš, F.; Achelle, S.; Barsella, A.; Kvashnin, Y.A.; Rusinov, G.L.; Charushin, V.N. 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. Molecules 2022, 27, 4250. https://doi.org/10.3390/molecules27134250

AMA Style

Verbitskiy EV, le Poul P, Bureš F, Achelle S, Barsella A, Kvashnin YA, Rusinov GL, Charushin VN. 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. Molecules. 2022; 27(13):4250. https://doi.org/10.3390/molecules27134250

Chicago/Turabian Style

Verbitskiy, Egor V., Pascal le Poul, Filip Bureš, Sylvain Achelle, Alberto Barsella, Yuriy A. Kvashnin, Gennady L. Rusinov, and Valery N. Charushin. 2022. "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" Molecules 27, no. 13: 4250. https://doi.org/10.3390/molecules27134250

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