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“固有手性”离子液体介质:在手性电极上进行有效的手性电化学分析。

"Inherently Chiral" Ionic-Liquid Media: Effective Chiral Electroanalysis on Achiral Electrodes.

机构信息

CNR, Istituto di Scienze e Tecnologie Molecolari (ISTM), Via Golgi 19, 20133, Milano, Italy.

Università degli Studi di Milano, Dipartimento di Chimica, Via Golgi 19, 20133, Milano, Italia.

出版信息

Angew Chem Int Ed Engl. 2017 Feb 13;56(8):2079-2082. doi: 10.1002/anie.201607344. Epub 2017 Jan 18.

Abstract

To achieve enantioselective electroanalysis either chiral electrodes or chiral media are needed. High enantiodiscrimination properties can be granted by the "inherent chirality" strategy of developing molecular materials in which the stereogenic element responsible for chirality coincides with the molecular portion responsible for their specific properties, an approach recently yielding outstanding performances as electrode surfaces. Inherently chiral ionic liquids (ICILs) have now been prepared starting from atropisomeric 3,3'-bicollidine, synthesized from inexpensive reagents, resolved into antipodes without need of chiral HPLC and converted into long-chain dialkyl salts with melting points below room temperature. Both the new ICILs and shorter family terms, solid at room temperature, employed as low-concentration additives in achiral ILs, afford impressive enantioselection for the enantiomers of different probes on achiral electrodes, regularly increasing with additive concentration.

摘要

要实现对映选择性电分析,需要使用手性电极或手性介质。通过开发分子材料的“固有手性”策略,可以赋予高对映选择性,其中负责手性的立体元素与负责其特定性质的分子部分重合,这种方法最近在电极表面上表现出了出色的性能。现在已经从对映异构的 3,3'-联吡啶开始制备固有手性离子液体(ICILs),该化合物由廉价试剂合成,无需手性 HPLC 即可拆分对映体,并转化为熔点低于室温的长链二烷基盐。新型 ICILs 和更短的家族术语,在室温下为固体,用作非手性 ILs 中的低浓度添加剂,在手性电极上对不同探针的对映异构体提供令人印象深刻的对映选择性,通常随着添加剂浓度的增加而增加。

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