Nanostructures from self-assembling triazine tertiary amine N-oxide amphiphiles

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Nanotechnology

Background:

• Amphiphilic molecules self-assemble into ordered structures in solution.
• Tertiary amine N-oxides are known surfactants, often forming micelles.
• Controlling self-assembly to form vesicles is crucial for encapsulation applications.

Purpose of the Study:

• To synthesize and characterize novel amphiphilic tertiary amine N-oxides.
• To investigate their self-assembly behavior in aqueous solutions.
• To explore the formation of vesicles and their potential for encapsulation.

Main Methods:

• Tensiometry
• Dynamic and static light scattering
• X-ray crystallography

Main Results:

• New amphiphilic tertiary amine N-oxides were successfully prepared.
• Hydrogen-bonded dimers were identified as primary assembly units.
• Vesicle formation was observed, contrasting with typical micelle formation of lauryl dimethylamine N-oxide (LDAO).
• A specific triazine derivative formed 1 μm vesicles capable of entrapping fluorescein.
• The [1,3,5]triazine core facilitated control over self-assembled structure sizes from nano- to micrometre scales.

Conclusions:

• Tertiary amine N-oxides can be designed to form vesicles through dimer assembly.
• The [1,3,5]triazine core offers a versatile platform for tuning the size of self-assembled structures.
• These findings open possibilities for novel drug delivery or encapsulation systems.