The objective of this study was to explore the role of enantiomers in the surface modification and adsorption process of polymers imprinted by chiral molecules. Here, R -, S - and R / S -1-aminoindanes ( T R , T S and T R / S ) were used as the model template molecules. Optimization of synthetic protocols facilitated preselection of the most efficient composition for a molecularly imprinted polymer (MIP)—methacrylic acid- co -ethylene glycol dimethacrylate—with satisfactory specificity and an imprinting factor equal to 3. This polymer composition was used further to analyse the effect of configuration of the template on adsorption properties. The results showed preferable adsorption of R -enantiomer, T R in the R -MIP and S -enantiomer, T S in the S -MIP but revealed variations in the binding capacities of T R and T S in the R - and S -cavity (stereoselectivity factor; k = 1.66 to 1.22, respectively). The theoretically analysed binding energies (Δ E B ) of both T R and T S in the R -cavity (Δ E B = − 506.14 to − 256.77 kcal mol −1 ) and S -cavity (Δ E B = − 302.42 to − 347.18 kcal mol −1 ) were in agreement with empirical data. Morphology and porosity analyses revealed the impact of the template molecule on the pore system of the MIP and control (a non-imprinted polymer), but enantiomers were only found to have a negligible role. Binding characterization revealed that the physisorption-governed adsorption process and Dubinin–Radushkevich model fitted the experimental data best. Finally, terahertz spectroscopy was employed to confirm the similarity between both materials imprinted by each enantiomer.

中文翻译：

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监测对映体在手性分子印迹聚合物的表面改性和吸附过程中的作用：理论与实践

本研究的目的是探索对映体在手性分子印迹的聚合物的表面改性和吸附过程中的作用。这里，R-、S-和R/S-1-氨基茚（TR、TS和TR/S）被用作模型模板分子。合成方案的优化有助于预先选择最有效的分子印迹聚合物 (MIP) 组合物——甲基丙烯酸-共聚乙二醇二甲基丙烯酸酯——具有令人满意的特异性和等于 3 的印迹因子。 该聚合物组合物用于进一步分析效果模板配置对吸附性能的影响。结果表明R-对映体、TR在R-MIP和S-对映体中的吸附较好，S-MIP 中的 TS 但揭示了 R 和 S 腔中 TR 和 TS 的结合能力的变化（立体选择性因子；k 分别为 1.66 至 1.22）。理论分析的TR和TS在R-腔（Δ EB = - 506.14至- 256.77 kcal mol -1 ）和S-腔（Δ EB = - 302.42至- 347.18 kcal mol -1）中的结合能（Δ EB ） ) 与经验数据一致。形态学和孔隙率分析揭示了模板分子对 MIP 和对照（非印迹聚合物）孔隙系统的影响，但发现对映异构体的作用可以忽略不计。结合表征表明物理吸附控制的吸附过程和 Dubinin-Radushkevich 模型最符合实验数据。最后，