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Related Experiment Videos

Hydrogen-bonding effects in calix

Cho1, Rudkevich, Shivanyuk

  • 1The Skaggs Institute for Chemical Biology and The Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 10, 2000
PubMed
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Self-assembling calixarene capsules with urea and amide groups form stable structures through hydrogen bonding. These supramolecular capsules exhibit unique encapsulation properties influenced by their rim substituents and dimerization.

Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Calixarenes are versatile macrocyclic hosts capable of forming self-assembled structures.
  • Hydrogen bonding plays a crucial role in directing the assembly and stability of supramolecular architectures.
  • Tailoring substituents on calixarene rims allows for fine-tuning of molecular recognition and encapsulation properties.

Purpose of the Study:

  • To synthesize and characterize novel self-assembling calix[4]arene based capsules (1a, 1b).
  • To investigate the role of urea and amide functionalities in directing capsule formation and stability.
  • To explore the encapsulation behavior and binding affinities of these novel capsules.

Main Methods:

  • Synthesis of calix[4]arene derivatives with urea and amide groups.

Related Experiment Videos

  • Spectroscopic characterization (NMR, IR) to confirm structure and self-assembly.
  • X-ray crystallography to elucidate solid-state structures.
  • Encapsulation studies in various nonpolar solvents and binary mixtures.
  • Heterodimerization experiments to assess binding interactions.

    • Main Results:

    • Successful synthesis and characterization of calix[4]arene capsules 1a and 1b featuring upper-rim urea and lower-rim amide groups.
    • Dimerization induces a perfect cone conformation stabilized by intramolecular amide hydrogen bonds, forming cycloenantiomeric seams.
    • Na+-cation complexation disrupts lower-rim hydrogen bonds but preserves the overall capsular assembly.
    • Amide groups significantly influence binding affinities compared to tetraester analogues.
    • Monomeric calixarenes adopt a pinched cone conformation, with solid-state studies revealing specific intramolecular and intermolecular hydrogen bonding networks.

    Conclusions:

    • The designed calix[4]arene capsules demonstrate controlled self-assembly driven by hydrogen bonding.
    • The interplay between upper-rim urea and lower-rim amide groups dictates capsule conformation, stability, and encapsulation properties.
    • These findings contribute to the development of sophisticated supramolecular hosts for molecular recognition and encapsulation.