Walczak Anna, Markiewicz Grzegorz, Gliński Michał, Čonková Miroslava, Stefankiewicz Artur R
Centre for Advanced Technologies, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 10, Poznań 61-614, Poland.
Faculty of Chemistry, Adam Mickiewicz University in Poznań, Uniwersytetu Poznańskiego 8, Poznań 61-614, Poland.
J Org Chem. 2025 Oct 17;90(41):14557-14564. doi: 10.1021/acs.joc.5c01500. Epub 2025 Oct 8.
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.
即使分子结构发生细微变化，超分子聚集体的形态也可能受到深刻影响。在本研究中，我们探究了氨基酸功能化的苯-1,3,5-三甲酰胺（BTA）衍生物的变化如何影响其在非极性溶剂中的自组装行为。具体而言，我们研究了连接基的灵活性、2,4,6位上庞大取代基引入的空间位阻以及中心核的性质（芳香族与脂肪族）所起的作用。我们的结果表明，这些结构变化导致了截然不同的聚集结果，从单体物种和不明确的低聚物到明确的纳米胶囊。这些发现突出了精确分子设计在控制超分子自组装中的重要性，并展示了特定结构因素如何决定所得材料的形态和性质。
