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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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 (glum value) of 0.003.

Original languageEnglish
Article numbere2100016
JournalHelvetica Chimica Acta
Volume104
Issue number4
DOIs
Publication statusPublished - 2021 Apr

Keywords

  • N−H/C−H coupling
  • circularly polarized luminescence
  • electron-deficient compounds
  • helicenes
  • hypervalent compounds
  • quinoxalines

ASJC Scopus subject areas

  • Catalysis
  • Biochemistry
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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