Circularly Polarized Luminescence Liquids Based on Siloxybinaphthyls: Best Binaphthyl Dihedral Angle in the Excited State

Kazuto Takaishi, Tomoki Matsumoto, Miyu Kawataka, Tadashi Ema

Research output: Contribution to journalArticlepeer-review

Abstract

A series of axially chiral 1,1′-binaphthyls with trialkylsiloxy (OSiR3) groups were synthesized. Among them, 1 a–c possessing OSiR3 groups at the 7,7′-positions and methyl groups at the 2,2′-positions were liquids at room temperature, and the neat liquids showed circularly polarized luminescence (CPL) (R=Bu; Φfl,liquid=0.21, |glum,liquid|=1.6×10−3). The |glum,liquid| value is the highest of pure liquids. These compounds remained liquid over a broad range of temperatures, down to −50 °C. Time-dependent DFT calculations indicated that in the excited state, the binaphthyls adopt a transoid conformation with a small angle between the electric and magnetic transition dipole moments (θμ,m=77°), which is a key factor in their CPL activity. The best binaphthyl dihedral angle in the excited state is approximately 110°.

Original languageEnglish
Pages (from-to)9968-9972
Number of pages5
JournalAngewandte Chemie - International Edition
Volume60
Issue number18
DOIs
Publication statusPublished - Apr 26 2021

Keywords

  • binaphthyls
  • circularly polarized luminescence
  • conformation analysis
  • fluorescence
  • liquids

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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