Cavity-containing aromatic oligoamide foldamers and macrocycles: progress and future perspectives

Area of Science:

• Supramolecular Chemistry
• Organic Chemistry
• Materials Science

Background:

• Aromatic oligoamide foldamers are a significant class of foldamers known for their rigidity and predictable conformations.
• Intramolecular hydrogen bonds stabilize these foldamers into crescent or helical structures with defined inner cavities.

Purpose of the Study:

• To explore the conformational diversity and applications of aromatic oligoamide foldamers and their macrocyclic derivatives.
• To investigate the design of foldamers for specific functions such as host-guest complexation, transmembrane transport, and anion binding.

Main Methods:

• Synthesis of aromatic oligoamide foldamers and macrocycles with varying backbone constraints.
• Structural characterization of foldamer conformations (e.g., helical, crescent).
• Investigation of host-guest interactions and transmembrane transport properties.

Main Results:

• Foldamers with fully constrained backbones adopt stable helical or crescent shapes with well-defined cavities.
• Macrocyclic derivatives exhibit persistent shapes and non-deformable cavities, acting as hosts and transmembrane channels.
• Partially constrained foldamers show solvent- or guest-dependent folding.
• Aromatic oligoamides with multiple NH donors are designed for adjustable anion binding.

Conclusions:

• Aromatic oligoamide foldamers and macrocycles are versatile scaffolds for creating functional supramolecular systems.
• Conformational control through backbone constraint is key to their predictable behavior.
• These systems show promise for applications in molecular recognition, sensing, and transport phenomena.