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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Authors: | Egor V Verbitskiy Pascal le Poul Filip Bure Sylvain Achelle Alberto Barsella Yuriy A Kvashnin Gennady L Rusinov Valery N Charushin |
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Abstract: | A series of novel V-shaped quinoxaline, 1,2,5]oxadiazolo3,4-b]pyrazine and 1,2,5]thiadiazolo3,4-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]Oxadiazolo3,4-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. |
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Keywords: | furazanopyrazine [1 2 5]thiadiazolo[3 4-b]pyrazine quinoxaline donor– acceptor systems twisted intramolecular charge transfer |
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