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

doi:10.1016/j.electacta.2016.12.169

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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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 language	English
Pages (from-to)	391-400
Number of pages	10
Journal	Electrochimica Acta
Volume	227
Early online date	7 Jan 2017
DOIs	https://doi.org/10.1016/j.electacta.2016.12.169
Publication status	Published - 10 Feb 2017

Bibliographical 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.

Keywords

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

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Accepted Manuscript
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.
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Cite this

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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.",

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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.",

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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.

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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.

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ER -

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

Abstract

Bibliographical note

Keywords

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