Reversible Chromatic Change of Supramolecular Gels for Visual and Selective Chiral Recognition of Histidine

Abstract

In the present work, a chemical reaction has been performed for supramolecular gels to achieve multiple-stimuli-responsive smart soft materials. Simple chiral binaphthalene-based receptors can condense with histidine (His) to yield a Schiff base, which would help to achieve visual chiral recognition of unprotected l/d-His through gel formation along with specific selectivity toward 20 amino acids. Through intermolecular hydrogen bonds, the resultant Schiff base molecules assemble with excess His molecules to form three-dimensional (3D) networks of metastable cross-linked nanospheres and stable nanofibers in EtOH/water and MeOH/water, respectively. Significantly, this condensation reaction exhibits unique reversible and chromatic phenomena between sol-gel phase transitions in EtOH/water, which provide a way to design chemical reaction-based multivisual-change supramolecular gels for sensing and switching applications.

Keywords: binaphthyls; chiral recognition; chromatic; reversible; supramolecular gels.