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Characterization of inherently chiral electrosynthesized oligomeric films by voltammetry and scanning electrochemical microscopy (SECM)

Donnici M.
•
Toniolo R.
•
Arnaboldi S.
altro
Daniele S.
2020
  • journal article

Periodico
MOLECULES
Abstract
A voltammetric and scanning electrochemical microscopy (SECM) investigation was performed on an inherently chiral oligomer-coated gold electrode to establish its general properties (i.e., conductivity and topography), as well as its ability to discriminate chiral electroactive probe molecules. The electroactive monomer (S)-2,20-bis(2,20-bithiophene-5-yl)-3,30-bibenzothiophene ((S)-BT2T4) was employed as reagent to electrodeposit, by cyclic voltammetry, the inherently chiral oligomer film of (S)-BT2T4 (oligo-(S)-BT2T4) onto the Au electrode surface (resulting in oligo-(S)-BT2T4-Au). SECM measurements, performed in either feedback or competition mode, using the redox mediators [Fe(CN)6]4− and [Fe(CN)6]3− in aqueous solutions, and ferrocene (Fc), (S)-FcEA, (R)-FcEA and rac-FcEA (FcEA is N,N-dimethyl-1-ferrocenylethylamine) in CH3CN solutions, indicated that the oligomer film, as produced, was uncharged. The use of [Fe(CN)6]3− allowed establishing that the oligomer film behaved as a porous insulating membrane, presenting a rather rough surface. This was inferred from both the approach curves and linear and bidimensional SECM scans, which displayed negative feedback effects. The oligomer film acquired semiconducting or fully conducting properties when the Au electrode was biased at potential more positive than 0.6 V vs. Ag|AgCl|KCl. Under the latter conditions, the approach curves displayed positive feedback effects. SECM measurements, performed in competition mode, allowed verifying the discriminating ability of the oligo-(S)-BT2T4 film towards the (S)-FcEA and (R)-FcEA redox mediators, which confirmed the results obtained by cyclic voltammetry. SECM linear scans indicated that the enantiomeric discriminating ability of the oligo-(S)-BT2T4 was even across its entire surface.
DOI
10.3390/molecules25225368
WOS
WOS:000594877600001
Archivio
http://hdl.handle.net/11368/2980755
info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-85096459067
https://doi.org/10.3390/molecules25225368
Diritti
open access
FVG url
https://arts.units.it/bitstream/11368/2980755/1/molecules-25-05368.pdf
Soggetti
  • Chiral electroactive ...

  • Electroanalysi

  • Enantiodiscrimination...

  • Inherently chiral oli...

  • Scanning electrochemi...

Web of Science© citazioni
2
Data di acquisizione
Mar 24, 2024
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