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|November 22, 2025
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Researchers explored dynamic chirality in expanded helicenes using chiral amine substituents. This novel method allows control over structure and chiroptic response, overcoming challenges in isolating single enantiomers.

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Area of Science:

  • Organic Chemistry
  • Nanomaterials Science
  • Chirality Studies

Background:

  • Expanded helicenes are chiral nanographenes with a unique screw-shaped structure.
  • Their inherent flexibility makes isolating single enantiomers challenging.
  • Dynamic chirality offers a method to control chiral systems.

Purpose of the Study:

  • To install chiral amine substituents into expanded [11]-helicenes.
  • To explore dynamic chirality in expanded helicenes.
  • To achieve a chiroptic response in expanded helicenes without conventional enantiomer resolution.

Main Methods:

  • Utilized mild, efficient, and reversible imine condensations.
  • Introduced chiral amine substituents into the cavity of a diformyl expanded [11]-helicene.
  • Investigated the chiroptical properties of the synthesized compounds.

Main Results:

  • Achieved strong molar circular dichroism (up to |Δε| = 300 M⁻¹ cm⁻¹) and absorption dissymmetry factors (|gabs| = 0.010).
  • Demonstrated that the magnitude of circular dichroism can be tuned by varying chiral amine substituents.
  • Correlated the chiroptic response to the diastereomeric ratios of the helicenes.

Conclusions:

  • This study presents the first instance of dynamic chirality in expanded helicenes.
  • The developed method offers a significant synthetic improvement over traditional enantiomer resolution techniques.
  • This approach provides a new avenue for controlling and observing chiroptic responses in nanographenes.