Synthesis and properties of an anthraquinone-based redox switch for molecular electronics

Elisabeth H. Van Dijk; Daniel J.T. Myles; Marleen H. Van Der Veen; Jan C. Hummelen

doi:10.1021/ol0606278

Synthesis and properties of an anthraquinone-based redox switch for molecular electronics

Elisabeth H. Van Dijk, Daniel J.T. Myles, Marleen H. Van Der Veen, Jan C. Hummelen^*

^*Corresponding author for this work

Molecular Energy Materials

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

128 Citations (Scopus)

Abstract

The synthesis of a molecular wire bearing an anthraquinone core and thioacetyl end groups for gold electrode binding is described. A model anthraquinone system, substituted with tert-butylthio groups, can be reversibly switched electrochemically from cross conjugated (low conductance "off") to linear conjugated (high conductance "on") via two-electron reduction/oxidation reactions. This feature holds promise for the anthraquinone-based wires to be used as redox-controlled switches in molecular electronic devices.

Original language	English
Pages (from-to)	2333-2336
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	11
DOIs	https://doi.org/10.1021/ol0606278
Publication status	Published - 25-May-2006

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abstract = "The synthesis of a molecular wire bearing an anthraquinone core and thioacetyl end groups for gold electrode binding is described. A model anthraquinone system, substituted with tert-butylthio groups, can be reversibly switched electrochemically from cross conjugated (low conductance {"}off{"}) to linear conjugated (high conductance {"}on{"}) via two-electron reduction/oxidation reactions. This feature holds promise for the anthraquinone-based wires to be used as redox-controlled switches in molecular electronic devices.",

author = "{Van Dijk}, {Elisabeth H.} and Myles, {Daniel J.T.} and {Van Der Veen}, {Marleen H.} and Hummelen, {Jan C.}",

year = "2006",

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AU - Van Dijk, Elisabeth H.

AU - Myles, Daniel J.T.

AU - Van Der Veen, Marleen H.

AU - Hummelen, Jan C.

PY - 2006/5/25

Y1 - 2006/5/25

N2 - The synthesis of a molecular wire bearing an anthraquinone core and thioacetyl end groups for gold electrode binding is described. A model anthraquinone system, substituted with tert-butylthio groups, can be reversibly switched electrochemically from cross conjugated (low conductance "off") to linear conjugated (high conductance "on") via two-electron reduction/oxidation reactions. This feature holds promise for the anthraquinone-based wires to be used as redox-controlled switches in molecular electronic devices.

AB - The synthesis of a molecular wire bearing an anthraquinone core and thioacetyl end groups for gold electrode binding is described. A model anthraquinone system, substituted with tert-butylthio groups, can be reversibly switched electrochemically from cross conjugated (low conductance "off") to linear conjugated (high conductance "on") via two-electron reduction/oxidation reactions. This feature holds promise for the anthraquinone-based wires to be used as redox-controlled switches in molecular electronic devices.

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DO - 10.1021/ol0606278

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VL - 8

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JO - Organic letters

JF - Organic letters

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ER -

Synthesis and properties of an anthraquinone-based redox switch for molecular electronics

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