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Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form

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 s...

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Autores principales: Bonetti, Giorgia, Arnaboldi, Serena, Grecchi, Sara, Appoloni, Giulio, Massolo, Elisabetta, Rossi, Sergio, Martinazzo, Rocco, Orsini, Francesco, Mussini, Patrizia R., Benincori, Tiziana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7249101/
https://www.ncbi.nlm.nih.gov/pubmed/32384781
http://dx.doi.org/10.3390/molecules25092175
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author Bonetti, Giorgia
Arnaboldi, Serena
Grecchi, Sara
Appoloni, Giulio
Massolo, Elisabetta
Rossi, Sergio
Martinazzo, Rocco
Orsini, Francesco
Mussini, Patrizia R.
Benincori, Tiziana
author_facet Bonetti, Giorgia
Arnaboldi, Serena
Grecchi, Sara
Appoloni, Giulio
Massolo, Elisabetta
Rossi, Sergio
Martinazzo, Rocco
Orsini, Francesco
Mussini, Patrizia R.
Benincori, Tiziana
author_sort Bonetti, Giorgia
collection PubMed
description 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 Naph(2)T(4) 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.
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spelling pubmed-72491012020-06-10 Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form Bonetti, Giorgia Arnaboldi, Serena Grecchi, Sara Appoloni, Giulio Massolo, Elisabetta Rossi, Sergio Martinazzo, Rocco Orsini, Francesco Mussini, Patrizia R. Benincori, Tiziana Molecules Article 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 Naph(2)T(4) 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. MDPI 2020-05-06 /pmc/articles/PMC7249101/ /pubmed/32384781 http://dx.doi.org/10.3390/molecules25092175 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Bonetti, Giorgia
Arnaboldi, Serena
Grecchi, Sara
Appoloni, Giulio
Massolo, Elisabetta
Rossi, Sergio
Martinazzo, Rocco
Orsini, Francesco
Mussini, Patrizia R.
Benincori, Tiziana
Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form
title Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form
title_full Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form
title_fullStr Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form
title_full_unstemmed Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form
title_short Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1′-Binaphthyl Selector Directly Synthesizable in Enantiopure Form
title_sort effective enantiodiscrimination in electroanalysis based on a new inherently chiral 1,1′-binaphthyl selector directly synthesizable in enantiopure form
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7249101/
https://www.ncbi.nlm.nih.gov/pubmed/32384781
http://dx.doi.org/10.3390/molecules25092175
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