Supramolecular microtubes based on 1,3,5-benzenetricarboxamides prepared by self-assembly upon heating

Area of Science:

• Supramolecular Chemistry
• Materials Science
• Organic Synthesis

Background:

• 1,3,5-Benzenetricarboxamides are versatile molecular building blocks.
• Controlling self-assembly in solution is crucial for designing functional materials.
• Tertiary amine substituents can influence solubility and self-assembly behavior.

Purpose of the Study:

• To synthesize and characterize a series of 1,3,5-benzenetricarboxamides with varying N,N-dialkyl-ethylamino substituents.
• To investigate the self-assembly behavior of these compounds in aqueous solutions upon thermal stimulation.
• To explore the formation of novel supramolecular structures.

Main Methods:

• Organic synthesis of three 1,3,5-benzenetricarboxamide derivatives.
• Characterization using standard spectroscopic techniques (NMR, Mass Spectrometry).
• Observation of self-assembly via heating in aqueous solution and subsequent structural analysis (e.g., microscopy).

Main Results:

• Successful synthesis of the target benzenetricarboxamide compounds.
• N¹,N³,N⁵-tris[2-(diethylamino)-ethyl]-1,3,5-benzenetricarboxamide demonstrated temperature-dependent phase separation from water.
• This compound self-assembled into well-defined, fiber-like supramolecular structures, specifically microtubes.

Conclusions:

• The length and nature of alkyl groups in the peripheral tertiary amine substituents significantly impact self-assembly.
• Heating aqueous solutions of specific benzenetricarboxamides can induce the formation of ordered supramolecular architectures.
• The observed microtube formation highlights the potential of these compounds for creating novel nanostructured materials.