A Stable Hexaazaoctacene Cruciform σ‐Dimer. Issue 27 (27th July 2022)

• Record Type: Journal Article
• Authors: Maier, Steffen; Jester, Fabian; Hoffmann, Marvin T.; Rominger, Frank; Freudenberg, Jan; Dreuw, Andreas; Bunz, Uwe H. F.
• Is Part Of: Advanced science. Volume 9:Issue 27(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-07-27
• Subjects: acenes -- azaoctacene -- biacenyl -- heteroacene -- octacene -- stabilization; Science -- Periodicals; 505
• DOI: 10.1002/advs.202202710
• Languages: English
• ISSNs: 2198-3844

Abstract

Abstract: Buchwald‐Hartwig coupling of a triisopropylsilyl (TIPS)‐ethynylated dibromo‐ N, N '‐dihydrotetraazapentacene with 1, 4‐bis(TIPS‐ethynyl)‐2, 3‐diaminonaphthalene furnishes a dihydrohexaazaoctacene. Its oxidation with MnO2 results in a 7, 7'‐bi(hexaazaoctacenyl). In addition to eight TIPS‐ethynyl groups, the bioctacene motif protects the azaoctacene subunits. The biazaoctacenyl displays a τ 1/2 of > 5 d in dilute solution under ambient conditions. In the crystalline state it is persistent for > 10 months. Abstract : In contrast to a triisopropylsilyl (TIPS)‐ethynylated hexaazaoctacene, its σ ‐dimer, a bihexaazaoctacenyl, is persistent in hexane and stable as a crystalline solid.