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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
Authors: Verbitskiy Egor V | le Poul Pascal | Bureš Filip | Achelle Sylvain | Barsella Alberto | Kvashnin Yuriy A | Rusinov Gennady L | Charushin Valery N
Year: 2022
Type of publication: článek v odborném periodiku
Name of source: Molecules
Publisher name: MDPI
Place: BASEL
Page from-to: 4250
Titles:
Language Name Abstract Keywords
cze Push-pull deriváty obsahující 2,4 '-bifenylenový linker a chinoxalin, [1,2,5]oxadiazolo[3,4-b]pyrazin a [1,2,5]thiadiazolo[3,4-b]pyrazin jako elektronakceptorní část Byla připravena série nových push-pull derivátů na bázi chinoxalinu, [1,2,5]oxadiazolo[3,4-b]pyrazinu a [1,2,5]thiadiazolo[3,4-b]pyrazinu s 2,4 '-bifenylenovým linkerem a byly studovány jejich elektrochemické, fotofyzikální a nelineárně optické vlastnosti. Experientální výsledky byly porovnány s teoretickými DFT kalkulacemi. furazanopyrazin; thiadiazolopyrazin; chinoxalin; donor-acceptorový systém;
eng 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 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. furazanopyrazine; [1; 2; 5]thiadiazolo[3; 4-b]pyrazine; quinoxaline; donor-acceptor systems; twisted intramolecular charge transfer

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