Host-Guest Complexation-Induced Aggregation Based on Pyrene-Modified Cyclodextrins for Improved Electronic Circular Dichroism and Circularly Polarized Luminescence

Angew Chem Int Ed Engl. 2022 Jul 18;61(29):e202203541. doi: 10.1002/anie.202203541. Epub 2022 May 17.

Abstract

Several γ-cyclodextrin (CD) derivatives mono- or di-substituted by pyrenes at the primary rim of the CD were demonstrated to aggregate into nano-strips in aqueous solutions, with the pyrene moieties interpenetrating into γ-CD cavities. The hydrophobic complexation-induced aggregation provides a rigid chiral environment for the pyrenes and leads to significant electronic circular dichroism (ECD) and circularly polarized luminescence (CPL) activities, giving unprecedently high gabs and glum values up to 4.3×10-2 and 5.3×10-2 , respectively. The aggregates lead to excimer emission with high quantum yields and show BCPL and BiCPL up to 338. 6 M-1 cm-1 and 169.3 M-1 cm-1 , respectively.

Keywords: Chiral Aggregation; Chiroptical Properties; Cyclodextrin; Host-Guest Complexation; Pyrene Excimer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Circular Dichroism
  • Cyclodextrins*
  • Electronics
  • Luminescence*
  • Pyrenes / chemistry

Substances

  • Cyclodextrins
  • Pyrenes
  • pyrene