Synthesis and metal binding properties of novel C2-symmetric tetraaza ligand systems

Abstract

This thesis describes the synthesis of novel Cz-symmetric tetramine ligands and an investigation of their metal binding properties via ftuorimetry and mass spectrometry. Chapter One provides an introduction to tetramine chemistry, discussing the synthesis and metal-binding properties of linear, cyclic and aromatic tetramines. It also highlights important ^plications of tetramines and their metal complexes in the areas of medicinal chemistry, catalysis of asymmetric synthesis and fluorescent sensing. Chapter Two is concerned with synthetic routes to two series of novel Cz-symmetric tetramine Hgands, based on naphthalene and pyridine. Optimisation of key steps in the synthetic route are discussed and opportunities to introduce chirality into the molecules are highlighted. Furthermore a two step route to tetramines, employing diamines and applicable to both series of ligands, is described. An efBcient route to a series of tetramines, both achiral and chiral, is achieved in both the naphthalene and pyridine series. The metal-binding properties of the tetramine Hgands are detailed in the following two sections. The fluorescence studies outlined in Chapter Three reveal the ef & cts of concentration, pH and the addition of metal ions on the fluorescence spectra of tetramines ligands in the naphthalene series. Mass spectrometry experiments are discussed in Chapter Four. This technique was shown to be suitable for observing the eflbcts of metal ion addition in both series of tetramines and permitted a comparison of Aeir metal binding aSinities. In both series of tetramines the ability to selectively bind metal ions, particularly copper, nickel, and palladium, was shown. In the concluding section. Chapter Five, the general experimental procedures and synthetic details are documented.

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