Synthesis of Hexaazatruxenes by Consecutive N−H/C−H Coupling Using a Hypervalent Iodine Reagent and Evaluation of Their Photophysical Properties

Yuchen Wu, Takuma Sasayama, Takahiro Gotoh, Mamoru Ito, Takanori Shibata*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

Truxene is a C3-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 N−H/C−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.

Original languageEnglish
Article numbere202200438
JournalEuropean Journal of Organic Chemistry
Volume2022
Issue number27
DOIs
Publication statusPublished - 2022 Jul 21

Keywords

  • Hypervalent compounds
  • Nitrogen heterocycles
  • Photoirradiation
  • Truxenes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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