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Twisted baskets.

Keith Hermann1, Yaowalak Pratumyot, Shane Polen

  • 1Department of Chemistry and Biochemistry, The Ohio State University, 100 West 18th Avenue (USA).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 22, 2015
PubMed
Summary
This summary is machine-generated.

Researchers developed a method to create chiral molecular baskets with specific twists. These twisted baskets, useful in supramolecular chemistry, show distinct self-inclusion properties enabling separation and exhibit strong fluorescence.

Keywords:
cavitandsencapsulationhost-guest systemsstereoselective recognitionsupramolecular chirality

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Chiral Materials

Background:

  • Development of chiral molecular architectures is crucial for advanced applications.
  • Tailoring host-guest chemistry requires precise control over molecular shape and chirality.

Purpose of the Study:

  • To develop a preparative procedure for chiral twisted molecular baskets.
  • To investigate the self-inclusion behavior and separation of enantiomers.
  • To characterize the absolute configuration and photophysical properties.

Main Methods:

  • Multi-step synthesis of racemic molecular baskets.
  • Chiral resolution via diastereomeric transesterification using (-)-menthol and a Ti(IV) catalyst.
  • Characterization using NMR spectroscopy, exciton chirality method, and DFT calculations.
  • Fluorescence spectroscopy to determine quantum yield.

Main Results:

  • A scalable synthesis for racemic twisted molecular baskets ((P/M)-1syn) was optimized.
  • Successful resolution into enantiomeric forms (8(P) and 8(M)) was achieved.
  • Differential self-inclusion of menthol moieties was observed, enabling chromatographic separation.
  • Absolute configurations were confirmed, and high fluorescence quantum yields were measured.

Conclusions:

  • The developed method provides access to enantiomerically pure chiral twisted molecular baskets.
  • The distinct self-inclusion properties facilitate effective separation of enantiomers.
  • The rigid, chiral framework and naphthalene chromophores result in strong fluorescence, suggesting potential applications in sensing or molecular devices.