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Vesicles and organogels from foldamers: a solvent-modulated self-assembling process.

Wei Cai1, Gui-Tao Wang, Yun-Xiang Xu

  • 1State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

Journal of the American Chemical Society
|May 14, 2008
PubMed
Summary

Non-amphiphilic foldamers self-assemble into vesicles in methanol and organogels in hydrocarbons. Flexible chains drive assembly through pi stacking and hydrogen bonding, forming distinct structures in different solvents.

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Area of Science:

  • Supramolecular chemistry
  • Materials science
  • Polymer chemistry

Background:

  • Nonamphiphilic molecules typically do not form self-assembled structures like vesicles.
  • Foldamers offer unique structural motifs for self-assembly.
  • Flexible chains can influence self-assembly behavior and material properties.

Purpose of the Study:

  • To investigate the self-assembly of nonamphiphilic, hydrogen-bonded hydrazide foldamers.
  • To characterize the structures formed in different solvent environments (polar vs. nonpolar).
  • To elucidate the driving forces behind the observed self-assembly.

Main Methods:

  • Scanning Electron Microscopy (SEM)
  • Atomic Force Microscopy (AFM)
  • Transmission Electron Microscopy (TEM)
  • Dynamic Light Scattering (DLS)
  • Fluorescence microscopy

Main Results:

  • Foldamers spontaneously assembled into one-layered vesicles in methanol.
  • Foldamers formed organogels in aliphatic hydrocarbons.
  • Assembly involved intermolecular pi stacking and hydrogen bonding, leading to cylindrical aggregates.
  • Vesicle formation in methanol was driven by hydrophobic entanglement of peripheral chains.
  • Organogel formation in hydrocarbons resulted from peripheral chains entangling across stacked cylinders.

Conclusions:

  • Nonamphiphilic foldamers can form complex self-assembled structures like vesicles and organogels.
  • Solvent polarity significantly dictates the resulting supramolecular architecture.
  • The interplay of pi stacking, hydrogen bonding, and flexible chain interactions governs the assembly process.