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

Author:

Mizukoshi Takato1,Sogawa Hiromitsu1ORCID,Sanda Fumio1ORCID

Affiliation:

1. Department of Chemistry and Materials Engineering Faculty of Chemistry, Materials and Bioengineering Kansai University 3-3-35 Yamate-cho, Suita Osaka 564-8680 Japan

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.

Funder

Japan Society for the Promotion of Science

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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