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Chiral spaces: dissymmetric capsules through self-assembly

J M Rivera1, T Martín, J Rebek

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.

Science (New York, N.Y.)
|March 7, 1998
PubMed
Summary

Symmetrical molecules self-assemble via hydrogen bonding into capsules with unique, dissymmetric cavities. These host molecular guests, with chiral recognition influencing cavity formation, observable in real-time using nuclear magnetic resonance.

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Area of Science:

  • Supramolecular Chemistry
  • Chemical Physics

Background:

  • Molecules with self-complementary surfaces assemble via intermolecular forces, often yielding unique properties.
  • Hydrogen bonding is a key interaction in the formation of self-assembled structures.

Purpose of the Study:

  • To describe systems where symmetrical molecules form capsules with dissymmetric cavities through hydrogen bonding.
  • To investigate the host-guest chemistry and chiral recognition capabilities of these self-assembled capsules.

Main Methods:

  • Utilizing hydrogen bonding for molecular self-assembly.
  • Employing nuclear magnetic resonance (NMR) spectroscopy for real-time observation of capsule formation and dissociation.
  • Investigating molecular recognition of chiral guests, including terpenes.

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Main Results:

  • Symmetrical molecules successfully assembled into capsules possessing dissymmetric cavities.
  • Capsule formation and dissipation were observed on a timescale amenable to NMR.
  • The capsules demonstrated host-guest behavior, accommodating smaller molecular guests.
  • Chiral recognition of guests, such as terpenes, influenced the preferential formation of specific dissymmetric cavities.

Conclusions:

  • Self-assembly driven by hydrogen bonding can yield complex supramolecular architectures like capsules with tunable internal environments.
  • The dynamic nature of these capsules, observable by NMR, allows for direct study of assembly processes.
  • Chiral molecular recognition is a critical factor in controlling the outcome of supramolecular assembly, enabling the selective formation of dissymmetric host structures.