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Electrochemical measurement of switchable hydrogen bonding in an anthraquinone-based anion receptor

Electrochemical measurement of switchable hydrogen bonding in an anthraquinone-based anion receptor
Electrochemical measurement of switchable hydrogen bonding in an anthraquinone-based anion receptor
The electrochemistry of a novel anion receptor is presented. The receptor 1,3-diphenylcarboxamidoanthraquinone (AAR) in the absence of an appropriate anion behaves as an anthraquinone system in the presence of a strong hydrogen bond donor. In this case, the electrochemical evidence supports the suggestion that the hydrogen bonding with the anthraquinone occurs at least partially through intra- or intermolecular interactions. It is suggested that these interactions stabilise both the semiquinone and dianion species resulting from reduction of AAR. However, in the presence of a suitable competitive anion (specifically F?), the hydrogen-bond donor groups bind to the anion rather than the quinone oxygen atoms. This removes the hydrogen bonding interaction to the redox-active quinone centre and hence alters the electrochemistry significantly. In the presence of F?, two one-electron quasireversible electrochemical processes are observed.
anion receptor, hydrogen bonding, fluoride, switchable electrochemistry, benzofuran-6, 11-dione derivatives, chloroflexus-aurantiacus, exogenous quinones, urea, recognition, reduction, electron, binding, design, agents
1388-2481
1351-1356
Brooks, Simon J.
fcf66c9a-5e4d-47cf-bc9f-e7c8886a061a
Birkin, Peter R.
69bea3c0-7dc2-42ed-89c9-59150746f392
Gale, Philip A.
ce0aa62f-d081-408b-8b00-6d954058afab
Brooks, Simon J.
fcf66c9a-5e4d-47cf-bc9f-e7c8886a061a
Birkin, Peter R.
69bea3c0-7dc2-42ed-89c9-59150746f392
Gale, Philip A.
ce0aa62f-d081-408b-8b00-6d954058afab

Brooks, Simon J., Birkin, Peter R. and Gale, Philip A. (2005) Electrochemical measurement of switchable hydrogen bonding in an anthraquinone-based anion receptor. Electrochemistry Communications, 7 (12), 1351-1356. (doi:10.1016/j.elecom.2005.10.022).

Record type: Article

Abstract

The electrochemistry of a novel anion receptor is presented. The receptor 1,3-diphenylcarboxamidoanthraquinone (AAR) in the absence of an appropriate anion behaves as an anthraquinone system in the presence of a strong hydrogen bond donor. In this case, the electrochemical evidence supports the suggestion that the hydrogen bonding with the anthraquinone occurs at least partially through intra- or intermolecular interactions. It is suggested that these interactions stabilise both the semiquinone and dianion species resulting from reduction of AAR. However, in the presence of a suitable competitive anion (specifically F?), the hydrogen-bond donor groups bind to the anion rather than the quinone oxygen atoms. This removes the hydrogen bonding interaction to the redox-active quinone centre and hence alters the electrochemistry significantly. In the presence of F?, two one-electron quasireversible electrochemical processes are observed.

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More information

Published date: 2005
Keywords: anion receptor, hydrogen bonding, fluoride, switchable electrochemistry, benzofuran-6, 11-dione derivatives, chloroflexus-aurantiacus, exogenous quinones, urea, recognition, reduction, electron, binding, design, agents

Identifiers

Local EPrints ID: 20737
URI: http://eprints.soton.ac.uk/id/eprint/20737
ISSN: 1388-2481
PURE UUID: b5b1b096-93c3-4c3f-8895-a930863d5c8e

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Date deposited: 02 Mar 2006
Last modified: 15 Jul 2019 19:25

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