Influence of Host-Guest Interaction between Chiral Selectors and Probes on the Enantioseparation Properties of Graphene Oxide Membranes.,ACS Applied Materials & Interfaces

当前位置： X-MOL 学术 › ACS Appl. Mater. Interfaces › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Influence of Host-Guest Interaction between Chiral Selectors and Probes on the Enantioseparation Properties of Graphene Oxide Membranes.
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2020-02-11 , DOI: 10.1021/acsami.0c00898
Chenchen Meng ₁ , Shaoze Zhang _{1,

2,

3} , Qibin Chen ₁ , Xiaoxiao Li ₁ , Honglai Liu ₁

Affiliation

Graphene oxide (GO)-based membranes have displayed superior performances in the chiral resolution compared with conventional polymer-based and inorganic membranes. However, the effect of the host-guest interaction between chiral selectors and probes on the enantioseparation properties of GO-based membranes remains to be established. In this work, l-phenylalanine (l-Phe, as the chiral selector)-modified GO-based (l-Phe-GO) membranes were fabricated, and their enantioseparation performances toward various enantiomers, that is, d- and l-phenylalanine (d- and l-Phe), d- and l-methionine (d- and l-Met), N-acyl-d-phenylalanine (N-acyl-d-Phe) and N-acyl-l-phenylalanine (N-acyl-l-Phe), and N-acyl-d-methionine (N-acyl-d-Met) and N-acyl-l-methionine (N-acyl-l-Met), were detected. Results show that (i) l-Phe is preferential to transport d-enantiomers relative to l-enantiomers; (ii) as far as d-enantiomers are concerned, the d-Phe-like enantiomers move faster than d-Met-like ones through the l-Phe-GO membrane owing to their different host-guest interactions. The strength of interactions between chiral selectors and probes was further confirmed from both experimental and theoretical standpoints. In the former case, the enantioselective adsorption of l-Phe-GO nanosheets toward the aforementioned enantiomers demonstrates that l-Phe delivers a higher adsorption capacity to d-enantiomers relative to l-enantiomers, and meanwhile, d-Phe-like enantiomers are better than d-Met-like enantiomers in the adsorption capacity. In the latter case, the chiral separation mechanism is clarified using the periodical density functional theory (DFT) calculation, indicating that l-Phe interacts with d-enantiomers more strongly than l-enantiomers. Especially, our calculations unveil that the difference in the interaction strength is principally dominated by the nonstereoselective interactions between chiral probes and the GO surface. Therefore, our findings suggest that the nonstereoselective weak interaction can be employed to improve the enantioselectivity of GO-based membranes.

中文翻译：

手性选择剂和探针之间的客体相互作用对氧化石墨烯膜的对映分离性能的影响。

与常规的基于聚合物的膜和无机膜相比，基于氧化石墨烯（GO）的膜在手性拆分方面表现出卓越的性能。然而，手性选择剂和探针之间的宿主-客体相互作用对基于GO的膜的对映分离性质的影响尚待确定。在这项工作中，制备了l-苯丙氨酸（l-Phe，作为手性选择剂）修饰的GO基（l-Phe-GO）膜，它们对各种对映异构体（即d-和l-苯丙氨酸）的对映体分离性能（d-和l-Phe），d-和l-蛋氨酸（d-和l-Met），N-酰基-d-苯丙氨酸（N-酰基-d-Phe）和N-酰基-1-苯丙氨酸（N检测了-酰基-1-Phe和N-酰基-D-蛋氨酸（N-酰基-d-Met）和N-酰基-1-蛋氨酸（N-酰基-1-Met）。结果表明：（i）l-Phe相对于l-对映体优先转运d-对映体；（ii）就d-对映体而言，由于它们与宿主-客体的相互作用不同，d-Phe-类对映体通过l-Phe-GO膜的移动速度快于d-Met-类。从实验和理论上都进一步证实了手性选择剂和探针之间相互作用的强度。在前一种情况下，l-Phe-GO纳米片对上述对映异构体的对映选择性吸附表明，相对于l-对映异构体，l-Phe对d-对映异构体具有更高的吸附能力，而d-Phe样对映异构体则更好。比d-Met样对映体的吸附能力强。在后一种情况下，使用周期密度泛函理论（DFT）计算阐明了手性分离机理，表明l-Phe与d-对映体的相互作用比l-对映体更强。特别是，我们的计算揭示了相互作用强度的差异主要由手性探针与GO表面之间的非立体选择性相互作用决定。因此，我们的发现表明，非立体选择性弱相互作用可以用来提高基于GO的膜的对映选择性。

更新日期：2020-02-21

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南