Push–Pull Derivatives Based on 2,4′-Biphenylene Linker with Quinoxaline, [1,2,5]Oxadiazolo[3,4-<i>B</i>]Pyrazine and [1,2,5]Thiadiazolo[3,4-<i>B</i>]Pyrazine Electron Withdrawing Parts
Egor V. Verbitskiy,
Pascal le Poul,
Filip Bureš,
Sylvain Achelle,
Alberto Barsella,
Yuriy A. Kvashnin,
Gennady L. Rusinov,
Valery N. Charushin
Affiliations
Egor V. Verbitskiy
I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620108 Ekaterinburg, Russia
Pascal le Poul
University Rennes, CNRS, Institut des Sciences Chimiques de Rennes—UMR 6226, 35000 Rennes, France
Filip Bureš
Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice Studenská 573, 53210 Pardubice, Czech Republic
Sylvain Achelle
University Rennes, CNRS, Institut des Sciences Chimiques de Rennes—UMR 6226, 35000 Rennes, France
Alberto Barsella
Département d’Optique Ultrarapide et Nanophotonique, IPCMS, UMR CNRS 7504, Université de Strasbourg, 23 rue du Loess, BP 43, CEDEX 2, 67034 Strasbourg, France
Yuriy A. Kvashnin
I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620108 Ekaterinburg, Russia
Gennady L. Rusinov
I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620108 Ekaterinburg, Russia
Valery N. Charushin
I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, 620108 Ekaterinburg, Russia
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.
