Polyazaacene and Cyclazaacene Precursors Synthesized by Dehydration Condensation from a Versatile Bis‐α‐diketone Unit Having an Anthracene Skeleton. Issue 38 (12th August 2022)

• Record Type: Journal Article
• Authors: Chan, Yee Seng; Hayashi, Hironobu; Sato, Shizuka; Kasahara, Shoma; Matsuo, Kyohei; Aratani, Naoki; Yamada, Hiroko
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 38(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-12
• Subjects: Cyclazaacene -- Dehydration condensation -- Polyazaacene -- Precursor approach -- Thermal conversion; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200621
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : Herein, 8, 11‐dihydro‐1, 4 : 8, 11‐diethanopentacene‐2, 3, 9, 10( 1H, 4H )‐tetraone was used as a versatile compound for synthesizing polyazaacene and cyclazaacene precursors. This modular strategy provides a novel pathway for generating polyazaacene precursors of varying lengths and cyclazaacene precursors of various sizes for being assessed by the powerful on‐surface chemistry.