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Durham e-Theses
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Flexible podand and metal-based hosts for anion binding and sensing

Dickson, Sara-Jane (2008) Flexible podand and metal-based hosts for anion binding and sensing. Doctoral thesis, Durham University.

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Abstract

A series of amino-pyridyl and aminomethyl-pyridyl ligands, all with both pyridyl and secondary amine functionalities have been synthesised. A new series of organic and metal- based derivatives of these ligands have been prepared, along with the preparation of an organic viologen host, with previously reported urea arms,(^1) and the properties of these new compounds, and in particular their anion binding behaviour have been studied. The 3-aminomethyl-pyridyl ligands interact with transition metals and anions, in both solution and the solid state. They showed a particular affinity for copper(II) salts, and a nitrate sensing system has been prepared using the Ligands fluorescence, through the addition of copper to a solution of the photo-active aminomethyl-pyridyl ligand. However, the active species has proved difficult to characterise. Ruthenium-based derivatives have been shown to form both 1:1 and 2:1 host: guest complexes with a variety of anions. These compounds have also shown an equilibrium in which anion binding promotes time-averaging of diastereotopic methylene protons. The addition of anions to the fluorescent sensing analogues has shown quenching of the fluorescence. Organic systems involving amino-pyridyl ligands around a di- and tri-substituted aryl core bind anions in solution. The fluorescent pyrene-derived host shows 2:1 host: guest binding in NMR spectroscopic studies, which is in contrast to work on aryl derivatives and previous work on anthracene containing hosts,(^2) which has shown 1:1 host: guest binding. Organic viologen compounds with urea arms and a control compound with pyridyl arms, show a colourimetric response to carboxylates, although in the presence of oxygen, decomposition occurs. These hosts also show an affinity for halide anions, which do not bring about this colourimetric response.

Item Type:Thesis (Doctoral)
Award:Doctor of Philosophy
Thesis Date:2008
Copyright:Copyright of this thesis is held by the author
Deposited On:08 Sep 2011 18:28

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