Synthesis of Three-Dimensional Butterfly Slit-Cyclobisazaanthracenes and Hydrazinobisanthenes through One-Step Cyclodimerization and Their Properties

Koji Yamamoto, Shuhei Higashibayashi

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

New three-dimensional (3D) π-conjugated molecules, butterfly-shaped slit-cyclobisazaanthracenes, were synthesized in high yields by Ni-mediated one-step cyclodimerization of dibromoazaanthracenes with a dimethylacridine, phenothiazine, or acridone skeleton. The 3D slit butterfly shape was formed by folded azaanthracene skeletons. Closure of the slit via N - N bond formation afforded hydrazinobisanthenes with an embedded hydrazine structure in a bisanthene skeleton, which exhibited a 3D butterfly or a 2D plane structure depending on the type of heterocycle used. Extensive study of the stereoselective chemical reactivity of the butterfly shape, X-ray analysis, DFT calculations, electrochemical/chemical oxidations, and photophysical measurements revealed that the properties of these materials included stereoselective oxidation, a rigid or flexible butterfly shape, dynamic conformational behavior, unique crystal-packing structures, excellent electron donation with low oxidation potential, a radical cation, a long absorption wavelength, and fluorescence property.

Original languageEnglish
Pages (from-to)663-671
Number of pages9
JournalChemistry - A European Journal
Volume22
Issue number2
DOIs
Publication statusPublished - 2016 Jan 11
Externally publishedYes

Keywords

  • cyclization
  • dimerization
  • hydrazine
  • nitrogen heterocycles

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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