# From Monomers to Nanocapsules: The Role of Structural Features in Amino-Acid-Derived BTA Self-Assembly

**Authors:** Anna Walczak, Grzegorz Markiewicz, Michał Gliński, Miroslava Čonková, Artur R. Stefankiewicz

PMC · DOI: 10.1021/acs.joc.5c01500 · The Journal of Organic Chemistry · 2025-10-08

## TL;DR

This paper explores how small changes in the structure of amino-acid-based molecules affect their self-assembly into different shapes like nanocapsules.

## Contribution

The study reveals how specific structural features control the formation of supramolecular assemblies from amino-acid-derived BTAs.

## Key findings

- Structural changes in BTA derivatives lead to different aggregation outcomes like monomers, oligomers, and nanocapsules.
- Linker flexibility and steric hindrance significantly influence self-assembly behavior.
- The central core's nature (aromatic vs aliphatic) affects the morphology of the assemblies.

## Abstract

The morphology of
supramolecular assemblies can be profoundly influenced
by even subtle changes in the molecular structure. In this study,
we investigate how variations in amino acid-functionalized benzene-1,3,5-tricarboxamide
(BTA) derivatives affect their self-assembly behavior in nonpolar
solvents. Specifically, we examine the roles of linker flexibility,
steric hindrance introduced by bulky substituents at the 2,4,6-positions,
and the nature of the central core (aromatic vs aliphatic). Our results
show that these structural changes lead to strikingly different aggregation
outcomes, ranging from monomeric species and ill-defined oligomers
to well-defined nanocapsules. These findings highlight the importance
of precise molecular design in controlling supramolecular self-assembly
and demonstrate how specific structural factors dictate the morphology
and properties of the resulting materials.

## Linked entities

- **Chemicals:** benzene-1,3,5-tricarboxamide (PubChem CID 448554)

## Full-text entities

- **Chemicals:** Amino-Acid (MESH:D000596), BTA (MESH:C558700)

## Full text

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## Figures

7 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12538580/full.md

## References

56 references — full list in the complete paper: https://tomesphere.com/paper/PMC12538580/full.md

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Source: https://tomesphere.com/paper/PMC12538580