Enantioselective electroanalysis, which aims to discriminate the enantiomers of electroactive chiral probes in terms of potential difference, is a very attractive goal. To achieve this, its implementation is being studied for various "inherently chiral" selectors, either at the electrode surface or in the medium, yielding outstanding performance. In this context, the new inherently chiral monomer Naph2T4 is introduced, based on a biaromatic atropisomeric core, which is advantageously obtainable in enantiopure form without HPLC separation steps by a synthetic route hinging on enantiopure 2,2'-dibromo-1,1'-binaphthalenes. The antipodes of the new inherently chiral monomer can be easily electrooligomerized, yielding inherently chiral electrode surfaces that perform well in both cyclic voltammetry (CV) enantiodiscrimination tests with pharmaceutically interesting molecules and in magnetoelectrochemistry experiments.

Effective enantiodiscrimination in electroanalysis based on a new inherently chiral 1,1'-binaphthyl selector directly synthesizable in enantiopure form

Giorgia Bonetti;Giulio Appoloni;Tiziana Benincori
2020-01-01

Abstract

Enantioselective electroanalysis, which aims to discriminate the enantiomers of electroactive chiral probes in terms of potential difference, is a very attractive goal. To achieve this, its implementation is being studied for various "inherently chiral" selectors, either at the electrode surface or in the medium, yielding outstanding performance. In this context, the new inherently chiral monomer Naph2T4 is introduced, based on a biaromatic atropisomeric core, which is advantageously obtainable in enantiopure form without HPLC separation steps by a synthetic route hinging on enantiopure 2,2'-dibromo-1,1'-binaphthalenes. The antipodes of the new inherently chiral monomer can be easily electrooligomerized, yielding inherently chiral electrode surfaces that perform well in both cyclic voltammetry (CV) enantiodiscrimination tests with pharmaceutically interesting molecules and in magnetoelectrochemistry experiments.
1,1'-binaphtyl monomer; Chiral voltammetry; DOPA enantiodiscrimination; Electrodeposited films; Inherent chirality; Magnetoelectrochemistry; Tryptophan enantiodiscrimination;
Bonetti, Giorgia; Arnaboldi, Serena; Grecchi, Sara; Appoloni, Giulio; Massolo, Elisabetta; Rossi, Sergio; Martinazzo, Rocco; Orsini, Francesco; Mussini, Patrizia R.; Benincori, Tiziana
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2097218
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