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

Egor V. Verbitskiy (1, 2) , Sylvain Achelle (3) , Filip Bureš (4) , Pascal Le Poul (3) , Alberto Barsella (5) , Yuriy A. Kvashnin (2) , Gennady L. Rusinov (1, 2) , Françoise Robin-Le Guen (3) , Oleg N. Chupakhin (1, 2) , Valery N. Charushin (1, 2)

1 UrFU - Ural Federal University [Ekaterinburg]
2 UB RAS - Ural Branch of Russian Academy of Sciences
3 ISCR - Institut des Sciences Chimiques de Rennes
4 Faculty of Chemical Technology [University of Pardubice]
5 IPCMS - Institut de Physique et Chimie des Matériaux de Strasbourg

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.

Mots clés: donor–acceptor systems; fluorescence; intramolecular charge transfer; nitrogen heterocycles; nonlinear optic

Domaines: Chimie

Egor V. Verbitskiy, Sylvain Achelle, Filip Bureš, Pascal Le Poul, Alberto Barsella, et al.. Synthesis, photophysical and nonlinear optical properties of [1,2,5]oxadiazolo[3,4-b]pyrazine-based linear push-pull systems. Journal of Photochemistry and Photobiology A: Chemistry, 2021, 404, pp.112900. ⟨10.1016/j.jphotochem.2020.112900⟩. ⟨hal-02960376⟩