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Effective Enantiodiscrimination in Electroanalysis Based on a New Inherently Chiral 1,1'-binaphthyl Selector Directly Synthesizable in Enantiopure Form.

Authors :
Bonetti G
Arnaboldi S
Grecchi S
Appoloni G
Massolo E
Rossi S
Martinazzo R
Orsini F
Mussini PR
Benincori T
Source :
Molecules (Basel, Switzerland) [Molecules] 2020 May 06; Vol. 25 (9). Date of Electronic Publication: 2020 May 06.
Publication Year :
2020

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 Naph <subscript>2</subscript> T <subscript>4</subscript> 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.

Details

Language :
English
ISSN :
1420-3049
Volume :
25
Issue :
9
Database :
MEDLINE
Journal :
Molecules (Basel, Switzerland)
Publication Type :
Academic Journal
Accession number :
32384781
Full Text :
https://doi.org/10.3390/molecules25092175