Self-Sorting in Diastereomeric Mixtures of Functionalized Dipeptides

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Biomaterials

Background:

• Functionalized dipeptides can self-assemble into ordered structures.
• Chirality is a fundamental property influencing molecular interactions and self-assembly.
• Controlling self-assembly is key to designing advanced functional materials.

Purpose of the Study:

• To investigate self-sorting behavior in dipeptide-based gelators differing only in chirality.
• To determine the influence of chirality on micellar and gel states.
• To provide evidence for self-sorting across varying concentrations.

Main Methods:

• Preparation of two dipeptide-based gelators with single amino acid chirality difference.
• Small-angle neutron scattering (SANS) for structural analysis.
• Cryo-transmission electron microscopy (cryo-TEM) for visualizing self-assembled structures.

Main Results:

• Complete self-sorting was observed in both micellar (high pH) and gel (low pH) states.
• The chirality of a single amino acid was confirmed as the driving force for self-sorting.
• Self-sorting occurred consistently across a range of relative component concentrations.

Conclusions:

• Chiral dipeptides exhibit predictable self-sorting, enabling control over supramolecular architecture.
• The micellar structures at high pH dictate the gel network structures at low pH.
• This study demonstrates a robust method for designing complex self-assembled systems based on chirality.