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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.
Highlights
Enantioselective electroanalysis is a very attractive target, potentially enabling discrimination between enantiomers of electroactive chiral probes without preliminary separation steps
The key step in the synthesis of Naph2 T4 (Scheme 1, referring to the (R)-antipode case) is the functionalization of the atropisomeric core that was performed through a Suzuki Pd-mediated coupling reaction starting from the enantiopure 2,2’-dibromo-1,1’-binaphthalene, which was identified as the intermediate of choice due to its accessibility [14]
1,10 -binaphthyl-2,20 -diamine as a chiral intermediate, which is commercially available in both enantiopure forms at a reasonable price
Summary
Enantioselective electroanalysis is a very attractive target, potentially enabling discrimination between enantiomers of electroactive chiral probes without preliminary separation steps. In spite of their outstanding properties, a common drawback is that since all of the above monomers have been synthesized as racemates, expensive semi-preparative HPLC resolution on a chiral stationary phase was necessary to obtain them in the enantiopure form required to prepare the chiral electrode surfaces. In this context, we propose the new inherently chiral monomer Naph T4 (Figure 2), based on a biaromatic carbocyclic rather than biheteroaromatic atropisomeric core. This monomer can be can be obtained in enantiopure form by a synthetic route hinging on 1,10 -binaphthyl-2,20 -diamine as a chiral intermediate, commercially available in both enantiopure forms at reasonable price, or synthesizable as a racemate [9] and resolvable by fractional crystallization of the diastereomeric salts with enantiopure chiral acids [10]
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