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A Cyclotriveratrylene Solvent-Dependent Chiral Switch.

Louise Miton1, Élise Antonetti1, Diego García-López1

  • 1Aix Marseille Université, CNRS, Centrale Marseille, iSm2 UMR 7313, 13397, Marseille, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 13, 2023
PubMed
Summary
This summary is machine-generated.

Researchers developed a novel chiral molecular switch using a cyclotriveratrylene scaffold. Solvent choice controls the molecule

Keywords:
cage compoundschiralitycyclotriveratrylenemolecular switchsolvent effects

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Chiral molecular switches are essential for developing advanced chiral molecular machines.
  • Hemicryptophanes, based on cyclotriveratrylene (CTV) scaffolds, exhibit inherent chirality (M or P handedness) and typically adopt an 'out' configuration.

Purpose of the Study:

  • To design and synthesize a single-molecule chiral switch based on a CTV scaffold.
  • To demonstrate solvent-controlled chirality inversion in hemicryptophanes.
  • To explore the reversible oscillation between different chiral configurations.

Main Methods:

  • Synthesis of a novel cyclotriveratrylene-based hemicryptophane.
  • Characterization using Nuclear Magnetic Resonance (NMR), High-Performance Liquid Chromatography (HPLC), and Electronic Circular Dichroism (ECD).
  • Computational analysis including Density Functional Theory (DFT) and molecular dynamics simulations.

Main Results:

  • Solvents were shown to control the 'in' and 'out' configurations of the CTV unit.
  • A chiral switch was created, transitioning between (M/P)"in" and (P/M)"out" configurations.
  • Bulky aromatic solvents (e.g., 2-t-butylphenol) favor the "in" configuration, while polar aprotic solvents (e.g., acetone) favor the "out" configuration.

Conclusions:

  • A reversible, solvent-controlled chiral molecular switch based on a CTV scaffold was successfully developed.
  • This system demonstrates the potential for external stimuli (solvents) to precisely control molecular chirality.
  • The findings open new avenues for designing responsive chiral materials and molecular machines.