Self-Standing Membranes Consisting of Inherently Chiral Electroactive Oligomers: Electrosynthesis, Characterization and Preliminary Tests in Potentiometric Setups

Serena Arnaboldi, Daniele Vigo, Mariangela Longhi, Francesco Orsini, Sephira Riva, Sara Grecchi, Elena Giacovelli, Vittoria Guglielmi, Roberto Cirilli, Giovanna Longhi, Giuseppe Mazzeo, Tiziana Benincori, Patrizia R. Mussini

Research output: Contribution to journalArticlepeer-review

Abstract

Self-standing chiral electroactive synthetic membranes are presented, prepared by oxidative electro-oligomerization of a thiophene-based “inherently chiral” electroactive monomer on indium tin oxide (ITO) or fluorine-doped tin oxide (FTO) electrodes, followed by detachment of the electrodeposited thin films in aqueous solution. The membranes, possibly mesoporous, consist of a mixture of open and cyclic “inherently chiral” oligomers, that is, in which both chirality and electroactivity originate from the same source, and this is the main conjugated backbone featuring a tailored torsion. Such a combination can afford outstanding chirality manifestations. The electrosynthesis conditions significantly modulate the oligomer distribution. Racemate films are compared to enantiopure ones. Circular dichroism confirms that (R)- or (S)- enantiopure films are obtained, starting from the corresponding (R)- or (S)- enantiopure monomers. Reliable transmembrane potential readings are obtained in preliminary tests in ion-selective electrode (ISE)-like setups, consistent with those predicted considering the membrane features, offering a first step towards extension of the protocol to chiral experiments.

Original languageEnglish
Pages (from-to)4204-4214
Number of pages11
JournalChemElectroChem
Volume6
Issue number16
DOIs
Publication statusPublished - 2019

Keywords

  • chiral thiophene-based oligomers
  • enantiopure membranes
  • inherent chirality
  • potentiometric setups
  • self-standing electroactive chiral membranes

ASJC Scopus subject areas

  • Catalysis
  • Electrochemistry

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