Polyazaacene and Cyclazaacene Precursors Synthesized by Dehydration Condensation from a Versatile Bis-α-diketone Unit Having an Anthracene Skeleton
Yee Seng Chan, Dr. Hironobu Hayashi, Shizuka Sato, Shoma Kasahara, Dr. Kyohei Matsuo, Prof. Dr. Naoki Aratani, Prof. Dr. Hiroko Yamada
European Journal of Organic Chemistry
Azaacenes are acene analogs containing nitrogen atoms in their carbon-based molecular skeletons and are attracting significant attention because of their potential application in organic electronics. However, polyazaacenes have solubility and stability issues. In this study, we report a modular approach employing 8,11-dihydro-1,4 : 8,11-diethanopentacene-2,3,9,10(1H,4H)-tetraone (1) as a key compound for π-extension with commercially available materials to synthesize a series of polytetraazaacene thermal precursors. Exploiting this strategy, tetraazaheptacene, tetraazanonacene, and tetraazaundecacene precursors were successfully synthesized. Thermogravimetric analysis revealed that the tetraazanonacene precursor can be converted to its corresponding tetraazanonacene in a nitrogen atmosphere. To extend the applicability of this method, compound 1 was also used to synthesize the cyclazaacene precursor at 0.8 % yield. This approach provides a new perspective for exploring the synthesis of polyazaacene and cyclazaacene precursors by using a crucial key compound via dehydration condensation reactions.
Azaacenes, organic electronics,