Amino‐Acid Based Chiral Trisubstituted Benzimidazole Supramolecules: Synthesis and Self‐Assembling Behavior

Abstract

AbstractTrisubstituted 1,3,5‐tri(benzimidazolyl)benzene derivatives were synthesized from l‐alanine, l‐valine, d‐valine and glycine, and their self‐assembling behavior and stimuli‐response in solution and gel states were evaluated. Circular dichroism/UV‐vis absorption spectroscopic and dynamic light scattering measurements revealed that the compounds formed H‐aggregates via intramolecular hydrogen bonding and π‐π stacking interactions in nonpolar solvents such as CHCl3, whereas collapse of the aggregates was confirmed by MeOH addition. Quantum mechanical calculations and molecular dynamics simulations also supported aggregation in CHCl3. Rheological analysis and morphology observation revealed the formation of a fibril like structure by further assembling of aggregates at a high concentration in CHCl3.