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手性:用于设计电化学对映体分离的固有手性离子液体的非常规手性元素。

Helicity: A Non-Conventional Stereogenic Element for Designing Inherently Chiral Ionic Liquids for Electrochemical Enantiodifferentiation.

机构信息

Dipartimento di Ingegneria e Scienze Applicate, Università di Bergamo, Viale Marconi 5, 24044 Dalmine, Italy.

CSGI Bergamo R.U., Viale Marconi 5, 24044 Dalmine, Italy.

出版信息

Molecules. 2021 Jan 9;26(2):311. doi: 10.3390/molecules26020311.

DOI:10.3390/molecules26020311
PMID:33435346
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7828060/
Abstract

Configurationally stable 5-aza[6]helicene () was envisaged as a promising scaffold for non-conventional ionic liquids (IL)s. It was prepared, purified, and separated into enantiomers by preparative HPLC on a chiral stationary phase. Enantiomerically pure quaternary salts of with appropriate counterions were prepared and fully characterized. -octyl-5-aza[6]helicenium bis triflimidate () was tested in very small quantities as a selector in achiral IL media to perform preliminary electrochemical enantiodifferentiation experiments on the antipodes of two different chiral probes. The new organic salt exhibited outstanding enantioselection performance with respect to these probes, thus opening the way to applications in the enantioselective electroanalysis of relevant bioactive molecules.

摘要

构型稳定的 5-氮杂[6]轮烯()被设想为一种很有前途的非常规离子液体(IL)支架。它通过手性固定相的制备型 HPLC 进行制备、纯化和对映异构体分离。制备并充分表征了与合适的抗衡离子的具有对映纯的 季铵盐。作为手性选择剂,少量的-辛基-5-氮杂[6]轮烯双三氟甲磺酰亚胺盐()在非手性 IL 介质中进行了初步的电化学对映体拆分实验,以对两种不同手性探针的对映体进行实验。新型有机盐对这些探针表现出出色的对映选择性,从而为相关生物活性分子的对映选择性电分析中的应用开辟了道路。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/b5c506d43341/molecules-26-00311-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/0d235d6aa2c5/molecules-26-00311-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/18ac6e3eb4ce/molecules-26-00311-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/013db5195718/molecules-26-00311-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/5fdd35c08f3b/molecules-26-00311-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/3152a4c5ad32/molecules-26-00311-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/d39843d4e6dc/molecules-26-00311-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/e657c04690b4/molecules-26-00311-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/57c4542457e8/molecules-26-00311-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/1259363035ca/molecules-26-00311-g005a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/b5c506d43341/molecules-26-00311-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/0d235d6aa2c5/molecules-26-00311-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/18ac6e3eb4ce/molecules-26-00311-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/013db5195718/molecules-26-00311-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/5fdd35c08f3b/molecules-26-00311-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/3152a4c5ad32/molecules-26-00311-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/d39843d4e6dc/molecules-26-00311-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/e657c04690b4/molecules-26-00311-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/57c4542457e8/molecules-26-00311-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/1259363035ca/molecules-26-00311-g005a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/edbe/7828060/b5c506d43341/molecules-26-00311-g006.jpg

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Intense redox-driven chiroptical switching with a 580 mV hysteresis actuated through reversible dimerization of an azoniahelicene.通过氮杂螺旋烯的可逆二聚作用驱动,实现具有580 mV滞后的强烈氧化还原驱动的手性光开关。
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"Inherently Chiral" Ionic-Liquid Media: Effective Chiral Electroanalysis on Achiral Electrodes.
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