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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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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. |
format | Online Article Text |
id | pubmed-7249101 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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