Enantioselective Dynamic Self-Assembly of Histidine Droplets on Pillar[5]arene-Modified Interfaces

The self-assembly of macroscopic droplets on interfaces has attracted much attention and shown promising potential in the field of materials as a sensing or delivery system. Herein, we reported a new strategy to construct a d-tartaric acid-functionalized pillar[5]arene (d-TP5) interface for macroscopic differentiation of histidine enantiomers. At the molecular level, it has been proved that d-TP5 has the ability to distinguish between l-Histidine and d-Histidine (KL/KD = 4.6). Furthermore, a functional d-TP5 surface was constructed by a click reaction and characterized by contact angle measurements and attenuated total reflection-Fourier-transform infrared spectroscopy and X-ray photoelectron spectroscopy analyses. The d-TP5 surface exhibited the selective dynamic adhesion of l-His droplets on the tilted interface. It means that a d-TP5 surface can distinguish histidine enantiomers at a macrolevel. The amount of d/l-His absorbed by a d-TP5 surface and the morphology of His particles formed by removing the solvent have been investigated to prove that the self-assembly of His occurs on the d-TP5 surface. The possible mechanism has been discussed from host–guest interaction and chiral recognition. The proposed chiral material displays rapidly remarkable selectivity and is convenient to be utilized, which should be suitable for comprehending chiral recognition processing and applied to chiral recognition detection of histidine in a living body.