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Electrochemical Anion Recognition By Novel Ferrocenyl Imidazole Systems
Molecules 2002, 7, 861-866
molecules
ISSN 1420-3049
Electrochemical Anion Recognition By Novel Ferrocenyl
Imidazole Systems
Jean-Luc Thomas, Joshua Howarth* and Anthony M. Kennedy
School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland. Tel. (+353) 1
7005312, fax (+353) 1 700 5503,
* Author to whom correspondence should be addressed: e-mail: Joshua.howarth@dcu.ie
Received: 22 November 2002; in revised form: 3 December 2002 / Accepted: 4 December 2002 /
Published: 31 December 2002
Abstract: A novel class of anion receptors with with C-H···X- hydrogen bonding is
introduced and demonstrated for Cl-, Br-, NO3- and HSO4- recognition. Cyclic voltammetry
revealed that novel ferrocenylimidazolium salts, syntheses of which are briefly described,
selectively complex and electrochemically recognise guest anions. Futhermore, proton
NMR spectroscopy indicated the formation of 1:2 stoichiometric complexes with Cl-, Br-
and I- and 1:1 stoichiometric complexes with NO3- and HSO4-.
Keywords: Ferrocenylimidazolium salts; anion receptors; 1H-NMR titrations, cyclo-
voltammetry, recognition.
Introduction
The synthesis of receptors designed to coordinate anions is an area of intense current research
activity. This is because anions are known to play ubiquitous roles in both chemical and biochemical
processes. Indeed, they can act as substrates or cofactors for enzymes [1], and as nucleophiles, base,
redox agents and phase transfer catalysts. During the last few years, the combination of LA and NH
group as a hydrogen bond donor have been demonstrated to be essential components for anion
recognition [2], but more recently the ability of 1,3-disubstituted imidazolium cations to enter into
Molecules 2002, 7
862
hydrogen bonds with
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