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

Trisubstituted 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 .