Aggregation-Induced Emission and Circularly Polarized Luminescence Duality in Tetracationic Binaphthyl-Based Cyclophanes

Amine Garci, Seifallah Abid, Arthur H.G. David, Marcos D. Codesal, Luja Đorđević, Ryan M. Young, Hiroaki Sai, Laura Le Bras, Aurélie Perrier, Marco Ovalle, Paige J. Brown, Charlotte L. Stern, Araceli G. Campaña, Samuel I. Stupp, Michael R. Wasielewski, Victor Blanco, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Here, we report an approach to the synthesis of highly charged enantiopure cyclophanes by the insertion of axially chiral enantiomeric binaphthyl fluorophores into the constitutions of pyridinium-based macrocycles. Remarkably, these fluorescent tetracationic cyclophanes exhibit a significant AIE compared to their neutral optically active binaphthyl precursors. A combination of theoretical calculations and time-resolved spectroscopy reveal that the AIE originates from limited torsional vibrations associated with the axes of chirality present in the chiral enantiomeric binaphthyl units and the fine-tuning of their electronic landscape when incorporated within the cyclophane structure. Furthermore, these highly charged enantiopure cyclophanes display CPL responses both in solution and in the aggregated state. This unique duality of AIE and CPL in these tetracationic cyclophanes is destined to be of major importance in future development of photonic devices and bio-applications.

Original languageEnglish (US)
JournalAngewandte Chemie - International Edition
DOIs
StatePublished - Oct 4 2022

Keywords

  • Aggregation-Induced Emission
  • Chirality
  • Circularly Polarized Luminescence
  • Macrocycles
  • Optoelectronics

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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