(E)-2-(6-(4′-(Diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5(4H)-ylidene)-2-(6-(4′-(diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)acetonitrile

• DOI: 10.3390/m1714
• Publication Date: 2023-08-21T05:49:34Z
• Authors: Yuriy A. Kvashnin; Pavel A. Slepukhin; Denis A. Gazizov; Ekaterina F. Zhilina; Gennady L. Rusinov; Egor V. Verbitskiy; Valery N. Charushin
• Keywords: ORGANIC SEMICONDUCTORS; 2-CYANOACETIC ACID; 1,2,5-OXADIAZOLO[3,4-B]PYRAZINES; 1,2,5-oxadiazolo[3,4-<i>b</i>]pyrazines; organic semiconductors; Inorganic chemistry; 2-cyanoacetic acid; QD146-197

[1,2,5]Oxadiazolo[3,4-b]pyrazines are of great interest due to their promising photophysical and electrochemical properties, as well their potential use in a wide range of electronic devices. Herein, we report on the preparation of the unexpected product derived from the interaction of 2′-([1,2,5]oxadiazolo[3,4-b]pyrazin-5-yl)-N,N-diphenyl-[1,1′-biphenyl]-4-amine with 2-cyanoacetic acid under basic conditions. The resulting product was characterized using 1H and 13C NMR spectra, high resolution mass spectrometry, Fourier-transform infrared spectroscopy (FTIR), and X-ray diffraction analyses. Furthermore, its photophysical and electrochemical properties were studied using cyclic voltammetry, UV–Vis, and emission spectroscopy. The experimental results have been further rationalized through theoretical DFT calculations.