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

Abstract

Comprehensive Summary Chiral 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.

Synthesis and Characterization of a Novel Pillar[5]arene That can Undergo Single-Crystal-to-Single-Crystal (SCSC) Transformation★

“…单晶 到单晶的转变可以通过晶体对多种外部刺激(温度 [3][4] 、 光照 [5][6] 、 机械力 [6][7][8][9] 和蒸汽 [9][10][11] )的响应而实现, 已在传感 器 [12][13][14] 、吸附 [15][16][17][18] 、催化 [13] 、手性 [19] 、信息加密 [20] 和分 子机器 [21][22] 等领域展现了卓越的应用前景. 柱芳烃是一类具备柱状结构和独特空腔的大环分 子, 因其空腔结构赋予的主客体性质被广泛应用于超分 子化学和功能材料研究 [23][24][25][26][27][28][29][30][31][32][33] . 在本研究中, 为了构建具 有新型主客体功能的柱芳烃分子, 将吩噻嗪引入柱芳 烃, 成功合成了一种具有新型骨架结构的柱 [5]芳烃.…”