@article{garcia_pech_sommer_gorman_2019, title={Synthesis of 5,12-Diazapentacenes and Their Properties}, volume={84}, ISSN={["1520-6904"]}, url={https://doi.org/10.1021/acs.joc.9b01628}, DOI={10.1021/acs.joc.9b01628}, abstractNote={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.}, number={23}, journal={JOURNAL OF ORGANIC CHEMISTRY}, publisher={American Chemical Society (ACS)}, author={Garcia, Rosalva C. and Pech, Matthew J. and Sommer, Roger and Gorman, Christopher B.}, year={2019}, month={Dec}, pages={15079–15086} }