Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, China; University of Chinese Academy of Sciences, Beijing, China.
Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, China.
J Chromatogr A. 2019 Aug 30;1600:209-218. doi: 10.1016/j.chroma.2019.04.053. Epub 2019 Apr 22.
Graphene quantum dots (GQD) functionalized β-cyclodextrin (β-CD) and cellulose silica composites were first prepared and applied in HPLC as chiral stationary phases (CSP) to investigate the effect of GQDs on chiral separation. Through comparing the enantioseparation performance of GQDs functionalized β-CD or cellulose CSPs and unmodified β-CD or cellulose CSPs, we found GQDs enhanced the enantioseparation performance of nature β-CD, β-CD-3,5-dimethylphenylcarbamate derivative and cellulose-3,5-dimethylphenylcarbamate derivative. Molecular modeling was applied to understand and theoretically study the enhancement mechanism of GQDs for enantioseparation. According to molecular simulation results, GQDs provide extra interactions such as hydrophobic, hydrogen bond and π-π interaction when chiral selector interacts with enantiomers, which enhances the chiral recognition ability indirectly. The molecular simulation results showed a good agreement with the experimental results. Our work reveals the enhancement performance of GQDs for chiral separation, it can be expected that GQDs-based chiral composites and chiral GQDs have great prospect in chiral separation and other research fields such as asymmetric synthesis, chiral catalysis, chiral recognition and drug delivery.
石墨烯量子点(GQD)功能化β-环糊精(β-CD)和纤维素二氧化硅复合材料首先被制备并应用于 HPLC 作为手性固定相(CSP),以研究 GQD 对手性分离的影响。通过比较 GQD 功能化的β-CD 或纤维素 CSP 与未修饰的β-CD 或纤维素 CSP 的对映体分离性能,我们发现 GQD 增强了天然β-CD、β-CD-3,5-二甲基苯甲酰氨基衍生物和纤维素-3,5-二甲基苯甲酰氨基衍生物的对映体分离性能。分子模拟被应用于理解和理论研究 GQD 对手性分离增强的机制。根据分子模拟结果,当手性选择器与对映体相互作用时,GQD 提供了额外的相互作用,如疏水、氢键和π-π相互作用,这间接增强了手性识别能力。分子模拟结果与实验结果吻合较好。我们的工作揭示了 GQD 对手性分离的增强性能,预计基于 GQD 的手性复合材料和手性 GQD 在手性分离以及不对称合成、手性催化、手性识别和药物输送等其他研究领域具有广阔的前景。