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Updated: Jan 17, 2026
09:34
Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
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Homochirality- and Heterochirality-Controlled H- and J-Aggregation with Terminal Residue-Directed Supramolecular
Shunjie Cheng1, Hanting Wang1, Minghao Wang1
1Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang, Hebei 050024, China.
Langmuir : the ACS Journal of Surfaces and Colloids
|September 16, 2025
Summary
Researchers designed chiral azobenzene-based dipeptides to study molecular to supramolecular chirality transfer. Their stereochemistry dictates self-assembly into distinct nanostructures, offering design principles for chiral nanomaterials.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Transferring molecular chirality to supramolecular chirality is a key challenge.
- Azobenzene-based dipeptide amphiphiles are suitable model systems for studying chirality transfer.
- Understanding self-assembly mechanisms is crucial for designing advanced nanomaterials.
Purpose of the Study:
- To investigate the transfer of molecular chirality to supramolecular chirality in multichiral systems.
- To explore the role of stereochemical configuration in the self-assembly of azobenzene-based dipeptides.
- To establish design principles for programmable chiral nanomaterials.
Main Methods:
- Synthesis of azobenzene-based dipeptide amphiphiles with varying stereochemistry.
- Characterization of self-assembly behavior in aqueous media using circular dichroism (CD).
- Computational modeling including density functional theory (DFT) and molecular dynamics (MD) simulations.
Main Results:
- Chiral derivatives self-assembled in aqueous solutions, exhibiting distinct CD responses.
- Supramolecular chirality critically depended on the stereochemistry of glutamic acid residues.
- Homochiral dipeptides formed elongated fibrils, while heterochiral analogs yielded disordered aggregates.
Conclusions:
- Stereochemistry of terminal residues dictates the hierarchical chirality propagation and morphology.
- DFT and MD simulations elucidated the mechanism of stereochemical control in self-assembly.
- Provides fundamental insights and design strategies for creating tunable chiral nanomaterials.
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