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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Chiral Induction and Memory via Supramolecular Deracemization.

Robert Hein1,2, Eric Sidler1, Yohan Gisbert1

  • 1Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 3, Groningen, 9747 AG, The Netherlands.

Angewandte Chemie (International Ed. in English)
|August 5, 2025
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel dynamic molecular switch that can be controlled by light or redox stimuli. This switch enables a unique supramolecular deracemization process, creating stable chiral molecules and allowing for reversible chiral information transfer and orthogonal chiral memory.

Keywords:
Chiral inductionChiral memoryDeracemizationHost‐guest systemsMolecular switchOvercrowded alkene

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Area of Science:

  • Chemical Sciences
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Chirality is fundamental in nature, and controlling molecular chirality is crucial in chemistry.
  • Developing new methods for enantioselective synthesis is a significant challenge with broad applications.

Purpose of the Study:

  • To present a helically chiral dynamic molecular switch.
  • To demonstrate a novel supramolecular deracemization process for enantiomer formation.

Main Methods:

  • Utilizing light or redox stimuli to populate a symmetric metastable state in the molecular switch.
  • Employing a chiral ammonium guest to induce preferential enantiomer formation during relaxation.
  • Investigating the stability and properties of the formed chiral host and its oxidized dication.

Main Results:

  • The molecular switch's enantiomers are interconverted via a single symmetric metastable state.
  • A supramolecular deracemization process, triggered by a chiral guest, leads to preferential enantiomer formation.
  • The resulting chiral host is stable without the guest, enabling reversible chiral information transfer.
  • Oxidation yields a chiral dication with orthogonal chiral memory, insensitive to light.

Conclusions:

  • The developed molecular switch offers a new principle for controlling molecular chirality.
  • This work enables stable and reversible chiral information transfer and orthogonal chiral memory.
  • The findings have implications for asymmetric synthesis and the development of chiral materials.