Electrochemical Response of the Threading/de-threading Process of Calix[6]arene-based Pseudorotaxanes Anchored on Glassy Carbon Electrodes

Guido Orlandini, Jessica Groppi*, Andrea Secchi, Arturo Arduini, Jeremy D. Kilburn

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Citation (Scopus)
15 Downloads (Pure)

Abstract

The development of functional materials and smart surfaces has received tremendous attention in recent years. The anchoring of molecular machines and the transfer of their properties on to solid substrates may facilitate the design of new smart devices. Herein, we report an approach to the covalent modification of glassy carbon electrodes with electrochemically responsive tris(N-phenylureido)calix[6]arene-based pseudorotaxanes. The main focus of this study has been the electrochemically driven threading/de-threading process of the redox active dialkylviologen axial component of the supramolecular assemble. After the creation of an amine monolayer on the electrode, pseudorotaxane systems were generated at the surface using different approaches. It was revealed, through electrochemical investigations, that the reversibility of the threading/de-threading process of the axle depended on the nature of the alkyl substituents on the axle.

Original languageEnglish
Pages (from-to)391-400
Number of pages10
JournalElectrochimica Acta
Volume227
Early online date7 Jan 2017
DOIs
Publication statusPublished - 10 Feb 2017

Fingerprint

Rotaxanes
Glassy carbon
Axles
Electrodes
Functional materials
Amines
Monolayers
Substrates
calix(6)arene

Keywords

  • calixarene
  • electrochemically switchable Host-Guest system
  • glassy carbon electrode
  • pseudorotaxane and rotaxane
  • viologen

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Electrochemistry

Cite this

Electrochemical Response of the Threading/de-threading Process of Calix[6]arene-based Pseudorotaxanes Anchored on Glassy Carbon Electrodes. / Orlandini, Guido; Groppi, Jessica; Secchi, Andrea; Arduini, Arturo; Kilburn, Jeremy D.

In: Electrochimica Acta, Vol. 227, 10.02.2017, p. 391-400.

Research output: Contribution to journalArticle

Orlandini, Guido ; Groppi, Jessica ; Secchi, Andrea ; Arduini, Arturo ; Kilburn, Jeremy D. / Electrochemical Response of the Threading/de-threading Process of Calix[6]arene-based Pseudorotaxanes Anchored on Glassy Carbon Electrodes. In: Electrochimica Acta. 2017 ; Vol. 227. pp. 391-400.
@article{75548254a6964ecaaceaef9dfba43cd6,
title = "Electrochemical Response of the Threading/de-threading Process of Calix[6]arene-based Pseudorotaxanes Anchored on Glassy Carbon Electrodes",
abstract = "The development of functional materials and smart surfaces has received tremendous attention in recent years. The anchoring of molecular machines and the transfer of their properties on to solid substrates may facilitate the design of new smart devices. Herein, we report an approach to the covalent modification of glassy carbon electrodes with electrochemically responsive tris(N-phenylureido)calix[6]arene-based pseudorotaxanes. The main focus of this study has been the electrochemically driven threading/de-threading process of the redox active dialkylviologen axial component of the supramolecular assemble. After the creation of an amine monolayer on the electrode, pseudorotaxane systems were generated at the surface using different approaches. It was revealed, through electrochemical investigations, that the reversibility of the threading/de-threading process of the axle depended on the nature of the alkyl substituents on the axle.",
keywords = "calixarene, electrochemically switchable Host-Guest system, glassy carbon electrode, pseudorotaxane and rotaxane, viologen",
author = "Guido Orlandini and Jessica Groppi and Andrea Secchi and Arturo Arduini and Kilburn, {Jeremy D.}",
note = "Acknowledgements This work was partly supported by the Italian MIUR (PRIN 2010CX2TLM) and University of Parma. We thank Centro Interdipartimentale di Misure “G. Casnati” for NMR and Mass measurements. We are grateful to Dr. Marco Giannetto of the Department of Chemistry of the University of Parma for the electrochemical impedance measurements.",
year = "2017",
month = "2",
day = "10",
doi = "10.1016/j.electacta.2016.12.169",
language = "English",
volume = "227",
pages = "391--400",
journal = "Electrochimica Acta",
issn = "0013-4686",
publisher = "Elsevier Limited",

}

TY - JOUR

T1 - Electrochemical Response of the Threading/de-threading Process of Calix[6]arene-based Pseudorotaxanes Anchored on Glassy Carbon Electrodes

AU - Orlandini, Guido

AU - Groppi, Jessica

AU - Secchi, Andrea

AU - Arduini, Arturo

AU - Kilburn, Jeremy D.

N1 - Acknowledgements This work was partly supported by the Italian MIUR (PRIN 2010CX2TLM) and University of Parma. We thank Centro Interdipartimentale di Misure “G. Casnati” for NMR and Mass measurements. We are grateful to Dr. Marco Giannetto of the Department of Chemistry of the University of Parma for the electrochemical impedance measurements.

PY - 2017/2/10

Y1 - 2017/2/10

N2 - The development of functional materials and smart surfaces has received tremendous attention in recent years. The anchoring of molecular machines and the transfer of their properties on to solid substrates may facilitate the design of new smart devices. Herein, we report an approach to the covalent modification of glassy carbon electrodes with electrochemically responsive tris(N-phenylureido)calix[6]arene-based pseudorotaxanes. The main focus of this study has been the electrochemically driven threading/de-threading process of the redox active dialkylviologen axial component of the supramolecular assemble. After the creation of an amine monolayer on the electrode, pseudorotaxane systems were generated at the surface using different approaches. It was revealed, through electrochemical investigations, that the reversibility of the threading/de-threading process of the axle depended on the nature of the alkyl substituents on the axle.

AB - The development of functional materials and smart surfaces has received tremendous attention in recent years. The anchoring of molecular machines and the transfer of their properties on to solid substrates may facilitate the design of new smart devices. Herein, we report an approach to the covalent modification of glassy carbon electrodes with electrochemically responsive tris(N-phenylureido)calix[6]arene-based pseudorotaxanes. The main focus of this study has been the electrochemically driven threading/de-threading process of the redox active dialkylviologen axial component of the supramolecular assemble. After the creation of an amine monolayer on the electrode, pseudorotaxane systems were generated at the surface using different approaches. It was revealed, through electrochemical investigations, that the reversibility of the threading/de-threading process of the axle depended on the nature of the alkyl substituents on the axle.

KW - calixarene

KW - electrochemically switchable Host-Guest system

KW - glassy carbon electrode

KW - pseudorotaxane and rotaxane

KW - viologen

UR - http://www.scopus.com/inward/record.url?scp=85009091500&partnerID=8YFLogxK

U2 - 10.1016/j.electacta.2016.12.169

DO - 10.1016/j.electacta.2016.12.169

M3 - Article

AN - SCOPUS:85009091500

VL - 227

SP - 391

EP - 400

JO - Electrochimica Acta

JF - Electrochimica Acta

SN - 0013-4686

ER -