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Self-sorting chiral subcomponent rearrangement during crystallization.

Marie Hutin1, Christopher J Cramer, Laura Gagliardi

  • 1Department of Organic Chemistry, University of Geneva, 30 Quai Ernest Ansermet, 1211 Genève 4, Switzerland.

Journal of the American Chemical Society
|June 27, 2007
PubMed
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Chiral amines precisely control dicopper helicate twisting, inducing specific helical structures. Racemic mixtures surprisingly crystallize into single enantiomers, reversing upon dissolution.

Area of Science:

  • Coordination Chemistry
  • Supramolecular Chemistry
  • Chiral Induction

Background:

  • Dicopper double helicates are supramolecular complexes with potential applications in catalysis and materials science.
  • Controlling the helical twist of these complexes is crucial for their function.
  • Enantiopure subcomponents can influence the stereochemistry of supramolecular assemblies.

Purpose of the Study:

  • To investigate the effect of enantiopure 1-amino-2,3-propanediol on the chiral induction of dicopper double helicates.
  • To determine the helicity of the complex in solution and solid state.
  • To elucidate the electronic structure and color origin of these complexes.
  • To study the behavior of racemic amine subcomponents in helicate formation.

Main Methods:

Related Experiment Videos

  • Synthesis of dicopper double helicates with enantiopure and racemic 1-amino-2,3-propanediol.
  • Density Functional Theory (DFT) calculations for helicity determination.
  • X-ray crystallography for solid-state structure analysis.
  • Electronic structure calculations for color origin investigation.

Main Results:

  • Enantiopure 1-amino-2,3-propanediol perfectly induced the helicate's twist, with S amines yielding a Lambda helical twist.
  • DFT and X-ray crystallography confirmed the helical induction in solution and solid state, respectively.
  • Electronic structure calculations identified metal-to-ligand charge transfer as the origin of the deep green color, with a delocalized Cu2(3+) core in the excited state.
  • Racemic amine subcomponents formed a dynamic library that unexpectedly converted to a single enantiomeric pair upon crystallization.
  • This crystallization-induced diastereomeric resolution was reversible upon redissolution, involving ligand exchange and covalent imine metathesis.

Conclusions:

  • Enantiopure amino-diol subcomponents provide precise control over dicopper double helicate chirality.
  • The observed deep green color is attributed to specific electronic transitions within the complex.
  • Crystallization can act as a powerful method for resolving complex dynamic libraries of diastereomers.
  • The reversible nature of this resolution highlights the dynamic equilibria present in these systems.