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Self-sorting dimerization of tetraurea calix[4]arenes.

Damien Braekers1, Christelle Peters, Anca Bogdan

  • 1Coordination and Radiochemistry, University of Liège, Sart Tilman B16, B-4000 Liège, Belgium.

The Journal of Organic Chemistry
|December 25, 2007
PubMed
Summary

Self-complementary calixarenes form dimeric capsules with ammonium guests. Steric crowding of substituents dictates capsule composition, enabling predictable self-assembly for supramolecular chemistry applications.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Calix[4]arenes with urea functionalities are self-complementary molecules.
  • These molecules self-assemble in nonpolar solvents with ammonium salts to form dimeric capsules stabilized by hydrogen bonds.
  • Tetraethylammonium salts can be encapsulated as guests within these dimeric structures.

Purpose of the Study:

  • To investigate the factors controlling the selective formation of dimeric capsules from mixtures of substituted calix[4]arenes.
  • To establish rules for predicting capsule composition based on substituent steric properties.
  • To demonstrate the utility of electrospray mass spectrometry for analyzing self-assembled structures.

Main Methods:

  • Synthesis of various substituted calix[4]arenes with urea functionalities.
  • Self-assembly experiments in apolar solvents in the presence of tetraethylammonium salts.
  • Analysis of dimeric capsule formation and composition using electrospray mass spectrometry (ESI-MS).

Main Results:

  • The steric crowding of substituents on the urea groups dictates the selective formation of dimeric capsules.
  • Aromatic substituents and aliphatic chains (in mono-, di-, or tetraloop structures) influence the self-sorting process.
  • ESI-MS provided clear information on dimer stoichiometry and composition, outperforming NMR in this context.
  • Overlapping aliphatic loops and bulky groups can destabilize dimeric structures.

Conclusions:

  • Predictable self-assembly of well-defined dimeric capsules is achievable by controlling calixarene substituent sterics.
  • Electrospray mass spectrometry is a powerful tool for characterizing complex supramolecular assemblies.
  • This work provides a foundation for designing bespoke molecular capsules with controlled guest inclusion.