A series of planar-stereogenicity ferrocenes, important as chiral promoters in enantioselective catalysis, is here characterized in terms of relationships between structure and electronic properties. The enantiomers of six selected model cases are then successfully discriminated in voltammetry experiments on electrodes modified with electrodeposited inherently chiral oligomer films, in terms of significant potential differences, specular inverting probe or selector configuration. Small substituent changes do not alter the enantiomer peak sequence, but result in significant modulation of peak potential differences, looking consistent with the availability of chiral/selector matching elements. The present stereogenic plane case, combined with former ones involving stereogenic centres, axes and/or helices, shows that the inherent chirality strategy in electroanalysis can be effective with all four rigid stereogenic elements.

Widening the scope of “inherently chiral” electrodes: enantiodiscrimination of chiral electroactive probes with planar stereogenicity / S. Grecchi, S. Arnaboldi, M. Korb, R. Cirilli, S.R. Araneo, V. Guglielmi, G. Tomboni, M. Magni, T. Benincori, H. Lang, P.R. Mussini. - In: CHEMELECTROCHEM. - ISSN 2196-0216. - (2020). [Epub ahead of print]

Widening the scope of “inherently chiral” electrodes: enantiodiscrimination of chiral electroactive probes with planar stereogenicity

S. Grecchi
Primo
;
S. Arnaboldi
Secondo
;
S.R. Araneo;V. Guglielmi;M. Magni;P.R. Mussini
Ultimo
2020

Abstract

A series of planar-stereogenicity ferrocenes, important as chiral promoters in enantioselective catalysis, is here characterized in terms of relationships between structure and electronic properties. The enantiomers of six selected model cases are then successfully discriminated in voltammetry experiments on electrodes modified with electrodeposited inherently chiral oligomer films, in terms of significant potential differences, specular inverting probe or selector configuration. Small substituent changes do not alter the enantiomer peak sequence, but result in significant modulation of peak potential differences, looking consistent with the availability of chiral/selector matching elements. The present stereogenic plane case, combined with former ones involving stereogenic centres, axes and/or helices, shows that the inherent chirality strategy in electroanalysis can be effective with all four rigid stereogenic elements.
enantiodiscrimination in electroanalysis; chiral electrodes; chiral voltammetry; electroactive probes of chiral planarity; electrode surface modification with inherently chiral electroactive oligomers; 1,2-planar-chiral alkenylferrocenyl phosphanes of catalytic interest
Settore CHIM/02 - Chimica Fisica
Settore CHIM/06 - Chimica Organica
Settore CHIM/01 - Chimica Analitica
Enhancing VINCE (Versatile INherently Chiral Electrochemistry)
16-giu-2020
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/745294
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