Enhanced Chiral Recognition Abilities of Cyclodextrin Covalent Organic Frameworks via Chiral/Achiral Functional Modification,ACS Applied Materials & Interfaces

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Enhanced Chiral Recognition Abilities of Cyclodextrin Covalent Organic Frameworks via Chiral/Achiral Functional Modification
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2022-05-24 , DOI: 10.1021/acsami.2c05572
Xuehua Wang _{1,

2} , Jiaqi Wu _{1,

2} , Xue Liu _{1,

2} , Xin Qiu _{1,

2} , Liqin Cao _{1,

2} , Yibing Ji _{1,

2}

Affiliation

β-Cyclodextrin covalent organic frameworks (β-CD COFs) show great potential in enantioseparation due to their uniformly distributed chiral recognition sites and good chemical stability. The hydroxyl and amino groups of β-CD COFs enable facile post-modification to introduce the desired functionality into the frameworks. In this study, we perform post-modification of β-CD COF_BPDA with 1,4-butane sultone and [(3R,4R)-4-acetyloxy-2,5-dioxooxolan-3-yl] acetate to construct two kinds of novel functional β-CD COFs. The capillary columns prepared with these two functional β-CD COFs separated chiral dihydropyridines and fluoroquinolones with excellent selectivity and repeatability in capillary electrochromatography, while β-CD COF_BPDA-modified capillary columns did not present the chiral recognition ability for these drugs. The mechanism of chiral recognition and the enhanced enantioselectivity of functional β-CD COFs were further demonstrated by molecular docking simulation. The divergent chiral separation performances of β-CD COFs suggest that the introduction of functional groups enables the modification of β-CD COF properties and tuning of its chiral recognition abilities for the diversity of enantioseparation.

中文翻译：

通过手性/非手性功能修饰增强环糊精共价有机框架的手性识别能力

β-环糊精共价有机骨架（β-CD COFs）由于其均匀分布的手性识别位点和良好的化学稳定性，在对映体分离中显示出巨大的潜力。β-CD COFs 的羟基和氨基可以方便地进行后修饰，将所需的功能引入框架。在本研究中，我们用 1,4-丁内酯和 [(3 R ,4 R )-4-acetyloxy-2,5-dioxooxolan-3-yl] 乙酸酯对 β-CD COF _BPDA进行后修饰，构建了两个各种新型功能性β-CD COF。用这两种功能性 β-CD COF 制备的毛细管色谱柱分离手性二氢吡啶和氟喹诺酮类药物，在毛细管电色谱中具有出色的选择性和重现性，而 β-CD COF _BPDA- 改进的毛细管柱不具备这些药物的手性识别能力。通过分子对接模拟进一步证明了功能性β-CD COF的手性识别机制和增强的对映选择性。β-CD COFs 的不同手性分离性能表明，官能团的引入能够改变 β-CD COF 的性质并调整其手性识别能力以适应对映体分离的多样性。

更新日期：2022-05-24

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