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Tribenzo

Cantrill1, Fyfe, Heiss

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles 90095-1569, USA.

Organic Letters
|May 18, 2000
PubMed
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Dibenzylammonium (DBA+) ions form [2]pseudorotaxanes with tribenzo[27]crown-9 (TB27C9) via hydrogen bonding. Substituents on DBA+ ions significantly impact complex stability and formation kinetics.

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Dibenzylammonium (DBA+) ions can form inclusion complexes with macrocyclic hosts.
  • Tribenzo[27]crown-9 (TB27C9) is a macrocycle capable of complexing cationic guests.
  • Hydrogen bonding plays a crucial role in stabilizing supramolecular assemblies.

Purpose of the Study:

  • To investigate the formation and stability of [2]pseudorotaxanes between DBA+ ions and TB27C9.
  • To determine the effect of substituents on the DBA+ phenyl rings on complexation.
  • To analyze the kinetics of complex formation and dissociation.

Main Methods:

  • Synthesis of substituted Dibenzylammonium (DBA+) ions.
  • Complexation studies using tribenzo[27]crown-9 (TB27C9).
  • Spectroscopic techniques (e.g., NMR) to characterize pseudorotaxane formation and stability.

Related Experiment Videos

  • Kinetic experiments to measure complexation and dissociation rates.

    • Main Results:

    • [2]Pseudorotaxanes are successfully formed between DBA+ ions and TB27C9, stabilized by hydrogen bonding.
    • Electron-withdrawing substituents (e.g., pCO2Me) on DBA+ enhance complex stability compared to the parent DBA+ ion.
    • Complexes with substituted DBA+ ions exhibit slower equilibration rates than the parent complex.

    Conclusions:

    • The stability and kinetics of DBA+/TB27C9 pseudorotaxanes are tunable via substituents on the DBA+ ion.
    • Hydrogen bonding is the primary driving force for the observed complexation.
    • This work provides insights into the rational design of host-guest systems with controlled binding affinities and dynamics.