From cyclohexyl isocyanide and diaminomaleonitrile to functional 5-(alkylamino)-6-substituted pyrazine-2,3-dicarbonitriles: synthesis, X-ray structural elucidation, antimicrobial testing and OLED analysis

Source: PubMed Central Open Access, NCBI / U.S. National Library of Medicine

New derivatives of 5-(alkylamino)-6-aryl/alkylpyrazine-2,3-dicarbonitriles were successfully synthesized with good to moderate yields through the reaction of alkyl isocyanides with aryl/alkyl carbonyl chlorides, followed by the incorporation of diaminomaleonitrile. The fluorescence quantum yields () were calculated and the fluorescence behavior of the produced compounds was examined. The cyclic voltammograms of compound 12a and compounds 14–17 with pyrazine-2,3-dicarbonitrile fragments were measured and the compounds were used in the fabrication of OLEDs. The compounds were dispersed in a commercial 4,4′-bis(-carbazolyl)-1,10-biphenyl host material and used for the formation of the emissive layer of OLEDs in concentration-dependent experiments. The OLED with 15 wt% of the emitting derivative 6,6′-(1,4-phenylene)bis(5-(cyclohexylamino)pyrazine-2,3-dicarbonitrile) exhibited superior performance. The antibacterial and antifungal properties of the newly synthesized pyrazine-2,3-dicarbonitriles were evaluated. 5-(Alkylamino)-6-aryl/alkylpyrazine-2,3-dicarbonitriles were synthesized through the reaction of alkyl isocyanides with aryl/alkyl carbonyl chlorides, followed by the incorporation of DAMN. toc