First synthesis of new polycyclic systems from ortho-di(heteroaryl)-substituted furazanopyrazine derivatives by the Scholl reaction |
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| Affiliation: | 1. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620108 Ekaterinburg, Russian Federation;2. Institute of Chemical Engineering, Ural Federal University, 620002 Ekaterinburg, Russian Federation |
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| Abstract: | A facile synthetic protocol to hard-to-get polycyclic (hetero)-aromatic compounds annulated to [1,2,4]oxadiazolo[3,4-b]-pyrazine scaffold via the FeCl3-mediated intramolecular Scholl cross-coupling has been developed. Based on the electrochemical and photophysical measurements, the synthesized polycyclic systems may be regarded as narrow band-gap (from 1.42 to 1.89 eV) n-type organic semiconductors whose energy levels are comparable to those of the commercially available n-type semiconductors |
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| Keywords: | furazanopyrazines Scholl reaction organic semiconductors C–H functionalization polycyclic aromatic hydrocarbons iron trichloride |
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