Binaphthyl-Bridged Pyrenophanes: Intense Circularly Polarized Luminescence Based on a D2 Symmetry Strategy

Kazuto Takaishi, Sho Murakami, Fumiya Yoshinami, Tadashi Ema

Research output: Contribution to journalArticlepeer-review

Abstract

A series of D2-symmetric macrocycles composed of alternately linked pyrene and binaphthyl moieties (binaphthyl-bridged pyrenophanes) have been synthesized. Among them, a pyrenophane possessing ether linkers at the 2,7-positions of the pyrenes exhibited intense circularly polarized luminescence (CPL) with a |glum| value of 0.053. This value is by far the highest for excimers and was not sensitive to temperature, solvent, or concentration. The CPL originated from a twisting pyrene excimer, with the (R)-binaphthyl moieties producing a left-handed twist excimer, which exhibited (−)-CPL. The electric and magnetic transition dipole moments are perfectly parallel, which is the best relationship for strong CPL.

Original languageEnglish
Article numbere202204609
JournalAngewandte Chemie - International Edition
Volume61
Issue number27
DOIs
Publication statusPublished - Jul 4 2022

Keywords

  • Axial Chirality
  • Biaryls
  • Circularly Polarized Luminescence
  • Conformation Analysis
  • Excimers

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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