Synthesis of 5,12-Diazapentacenes and Their Properties
datasetposted on 2019-11-12, 23:30 authored by Rosalva C. Garcia, Matthew J. Pech, Roger Sommer, Christopher B. Gorman
An efficient synthesis via a precursor route to a new class of linear dialkyldiaminoazapentacenes is reported. The synthetic route involves the coupling of 4-substituted aniline derivatives to 2,5-dibromoterephthalonitrile via Buchwald–Hartwig amination followed by an acid-mediated cyclization to furnish the diazapentacenes. These reactions occur under short reaction times (<2 h), provide high yields (77–99%), and do not require column chromatography for purification. The electrochemical and optical properties of the diazapentacenes were evaluated, and the values indicate that these molecules are promising n-type materials for organic electronic devices. The photostability of these molecules was significantly greater than unsubstituted acenes. Their method of degradation via endoperoxide generation was confirmed by X-ray crystallography and mass spectrometry.
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endoperoxide generationmass spectrometrycolumn chromatographymethod4-unsubstituted acenesacid-mediated cyclizationPropertiesSynthesiprecursor routemoleculedialkyldiaminoazapentacenedegradationdibromoterephthalonitrileaminationX-ray crystallographydevicephotostabilityn-type materialsDiazapentaceneyieldpurificationaniline derivativesdiazapentaceneelectrochemicalsynthesisBuchwald