Synthesis and Chiroptical Properties of Quinoxaline‐Fused Polyaza[5]–[7]helicenes with Orange‐Color CPL Emissions
Takashi Otani, Takuma Sasayama, Masashi Horiuchi, Shunnosuke Okauchi, Hidetoshi Kawai, Maho Kitahara, Yoshitane Imai, Takanori Shibata
Abstract
Abstract 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 ( g lum value) of 0.003.
Topics & Concepts
QuinoxalineChemistryHelicenePhotochemistryHypervalent moleculeReagentChromophoreLuminescenceCircular dichroismOrange (colour)MoleculeStereochemistryOrganic chemistryOptoelectronicsFood sciencePhysicsSynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsPhotochromic and Fluorescence Chemistry