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

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2021-01, Vol.404, p.112900, Article 112900
• Main Authors: Verbitskiy, Egor V., Achelle, Sylvain, Bureš, Filip, le Poul, Pascal, Barsella, Alberto, Kvashnin, Yuriy A., Rusinov, Gennady L., Guen, Françoise Robin-le, Chupakhin, Oleg N., Charushin, Valery N.
• Format: Article
• Language: English
• Subjects: Chemical Sciences; donor–acceptor systems; fluorescence; intramolecular charge transfer; nitrogen heterocycles; nonlinear optic
• ISSN: 1010-6030; 1873-2666
• DOI: 10.1016/j.jphotochem.2020.112900

[Display omitted] •D-π-A chromophores based on [1,2,5]oxadiazolo[3,4-b]pyrazine electron-withdrawing group were designed.•The influence of the π-conjugated linker and the amino-electron-donating group was studied.•The second order nonlinear optical properties were also studied using EFISH method. A series of D-π-A chromophores based on [1,2,5]oxadiazolo[3,4-b]pyrazine electron-withdrawing group has been designed. The influence of the π-conjugated linker (1,4-phenylene and 2,5-thienylene) and the amino-electron-donating group (diphenylamino and carbazol-9-yl) was studied by cyclic voltammetry, UV-Vis and emission spectroscopy. The second order nonlinear optical properties were also studied using the electric field induced second harmonic generation (EFISH) method. The experimental results have been rationalized by theoretical DFT calculations.