We achieved a two‐type synthesis of quinoxaline‐fused polyaza[5]‐ and [7]helicenes through consecutive N−H/C−H coupling with a hypervalent iodine reagent as a key reaction. By fusing electron‐deficient quinoxaline, these polyazahelicenes constitute an efficient donor‐acceptor type of molecule with absorption edges that reach up to approximately 650 nm. Evaluating the chiroptical properties reveals that the polyazahelicene exhibits a rare orange circularly polarized glow with a luminescence dissymmetry factor (glum value) of 0.003.
Truxene is a C 3 -symmetric compound with characteristic photophysical properties, and it has great potential as a light-emitting material and building block. In this study, we demonstrate the synthesis of hexaazatruxenes using a two-step protocol. First, the hexaazatruxene precursors were prepared through the Buchwald-Hartwig amination of 1,3,5-tribromobenzene with commercially available or easily prepared amino-pyridine derivatives. Then, hexaazatruxenes were synthesized through consecutive NÀ H/CÀ H coupling using a hypervalent iodine reagent. To the best of our knowledge, this is the first report on the synthesis of truxenes containing more than three heteroatoms in the main skeleton.
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