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A simple synthetic route to hard-to-prepare polycyclic (hetero)aromatic compounds with the [1,2,5]chalcogenodiazolo[3,4-b]pyrazine scaffold was developed based on the intramolecular nucleophilic aromatic hydrogen substitution reaction. Electrochemical and photophysical measurements demonstrated that the synthesized polycyclic systems can be considered as narrow-bandgap (from 1.25 to 1.44 eV) n-type organic semiconductors, the energy levels of which are comparable to those of commercially available electronic semiconductors. [ABSTRACT FROM AUTHOR]

The possibility of using push-pull systems based on furazanopyrazine in organic light-emitting diodes (OLEDs) and photovoltaic film devices was shown for the first time. The emission of all the obtained light-emitting diodes had a yellow-green color, and a maximum brightness of 45600 cd m−2 was achieved at a maximum current efficiency of 2.9 cd A−1. It was determined that the mobility of charge carriers measured in different current modes for these push-pull systems ranged from 10−4 to 4 · 10−6 cm2 V−1 s−1, considerably exceeding the values of the well-known compound Spiro-MeOTAD, widely used in high-efficiency photovoltaic devices. [ABSTRACT FROM AUTHOR]

5-(9-Ethyl-9H-carbazol-3-yl)-substituted 6-(het)aryl[1,2,5]oxadiazolo[3,4-b]pyrazines were synthesized by direct transition metal-free C—H functionalization in the pyrazine ring. Their photophysical and sensory properties with respect to nitrobenzene and 2,4-dinitrotoluene vapors were studied using a Nitroscan portable detector of nitro-explosive substances (Ekaterinburg, Russia). [ABSTRACT FROM AUTHOR]

Stable σH-adducts of O- and C-nucleophiles were obtained with cations of 5-(het)aryl-2,3-dicyano-1-ethylpyrazinium, and their structure was investigated by X-ray diffraction analysis. Analytical separation was performed of 1,2-dihydropyrazines into individual enantiomers by means of HPLC on columns with chiral sorbents. [ABSTRACT FROM AUTHOR]

The O- and C-adducts of 5-aryl and 5-hetaryl-2,3-dicyano-1-ethylpyrazinium salts are hidden sources of ylides, which can be used for the cyclization with arylacetylenes giving rise to pyrrolo[1,2- a]pyrazines. [ABSTRACT FROM AUTHOR]