Bipolar Electrochemical Measurement of Enantiomeric Excess with Inherently Chiral Polymer Actuators

Serena Arnaboldi , Gerardo Salinas , Giorgia Bonetti , Roberto Cirilli , Tiziana Benincori , Alexander Kuhn (1)

1 Bordeaux INP - Institut Polytechnique de Bordeaux

Straightforward enantioselective analytical methods are very important for drug safety, considering that in certain cases one of the two enantiomers of a chiral molecule might be harmful for humans. In this work, we propose a simple system for the direct and easy read-out of the enantiomeric excess of 3,4-dihydroxyphenylalanine (DOPA) as a model analyte. A conducting oligomer, i.e. oligo-(3,3′-dibenzothiophene), bearing inherently chiral features, is electrogenerated on a polypyrrole film. The resulting freestanding hybrid material is used as a wireless enantioselective actuator in a bipolar electrochemical cell. Combining in a single setup two individual actuators with opposite chiral features allows a direct visual read-out of enantiomeric excess, as the bending amplitude of each of the two actuators is directly correlated with the concentration of the corresponding stereoisomer of the analyte. Optimization of the experimental parameters results in efficient bending, giving access to the percentage values of the enantiomeric excess in mixtures containing different ratios of the antipodes, thus opening the way to potential applications for chiral in situ analysis.

Mots clés: Metrics & More Article Recommendations Electrochemical Actuators; Direct Enantiomeric Excess Determination; Inherent Chirality; Absolute Enantiodiscrimination; Bipolar Electrochemistry

Domaines: Chimie

Serena Arnaboldi, Gerardo Salinas, Giorgia Bonetti, Roberto Cirilli, Tiziana Benincori, et al.. Bipolar Electrochemical Measurement of Enantiomeric Excess with Inherently Chiral Polymer Actuators. ACS Measurement Science Au, 2021, 1 (3), pp.110 - 116. ⟨10.1021/acsmeasuresciau.1c00011⟩. ⟨hal-03516200⟩