Facile Synthesis of Azahelicenes and Diaza[8]circulenes through the Intramolecular Scholl Reaction

Chihiro Maeda, Shuichi Nomoto, Koki Akiyama, Takayuki Tanaka, Tadashi Ema

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Carbazole-based aza[7]helicenes and hetero[9]helicenes were successfully obtained via the intramolecular Scholl reaction of 3,6-bis(biphenyl-2-yl)carbazole congeners, while the reaction of 3,6-bis(naphthylphenyl)-appended carbazole gave a triple helicene via an unexpected simultaneous double aryl rearrangement. DFT calculations suggested that the rearrangement proceeded via an arenium cation intermediate. In addition, the reaction of methoxy-appended substrate gave an azahepta[8]circulene via the concurrent C−C bond formation. These helical dyes showed circularly polarized luminescence. The azahepta[8]circulene was further transformed into deeply saddle-distorted dibenzodiaza[8]circulenes as the first example of its solution-based synthesis and unambiguous structural determination.

Original languageEnglish
Pages (from-to)15699-15705
Number of pages7
JournalChemistry - A European Journal
Volume27
Issue number63
DOIs
Publication statusPublished - Nov 11 2021

Keywords

  • carbazoles
  • circularly polarized luminescence
  • circulenes
  • dyes
  • helicenes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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