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.

Bipolar Electrochemical Measurement of Enantiomeric Excess with Inherently Chiral Polymer Actuators / S. Arnaboldi, G. Salinas, G. Bonetti, R. Cirilli, T. Benincori, A. Kuhn. - In: ACS MEASUREMENT SCIENCE AU. - ISSN 2694-250X. - 1:(2021 Jul 19), pp. 110-116. [10.1021/acsmeasuresciau.1c00011]

Bipolar Electrochemical Measurement of Enantiomeric Excess with Inherently Chiral Polymer Actuators

S. Arnaboldi
Primo
;
2021

Abstract

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.
Electrochemical Actuators; Direct Enantiomeric Excess Determination; Inherent Chirality; Absolute Enantiodiscrimination; Bipolar Electrochemistry;
Settore CHIM/01 - Chimica Analitica
Article (author)
File in questo prodotto:
File Dimensione Formato  
acsmeasuresciau.1c00011.pdf

accesso aperto

Tipologia: Publisher's version/PDF
Dimensione 6.06 MB
Formato Adobe PDF
6.06 MB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/888455
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact