Engineering and Application of Pillar[6]arene Functionalized Chiral Surface in Selective Adsorption of R‐Adrenaline

Abstract

Comprehensive SummaryChiral properties of biological surface is of importance as they dominate interactions with biomolecules (such as proteins, nucleic acids, hormones) in a living system. Inspired by this phenomenon, we designed and constructed a L‐/D‐N‐acetyl‐cysteine‐pillar[6]arene functionalized Si surface (L‐/D‐NACP surface) for studying the influence of superficial chirality on selective adsorption of R‐adrenaline. The fabricated chiral L‐/D‐NACP surface with consistency in hydrophilia and elementary composition exhibited a strong mirror‐symmetric circular dichroism signal. In the adsorption study, the contact‐angle of R‐adrenaline droplet on D‐NACP surface was more hydrophilic from macroscopical view, and the size and quantity of R‐adrenaline aggregation on D‐NACP surface was larger than L‐NACP surface, implying selective adsorption of R‐adrenaline appeared on the D‐NACP surface. The possible mechanism was due to the stronger host‐guest interaction between D‐NACP and R‐adrenaline, which facilitated the selective adsorption. Besides, the D‐NACP surface with good selectivity can be used for chiral separation of racemic adrenaline. The results enhance the understanding of hormones adsorption affected by surface chirality, and may provide some helpful inspiration for practical application of chiral surface.