Polymer-supported pincers for selective molecular and ionic binding

Golden, Christopher Alex (2005) Polymer-supported pincers for selective molecular and ionic binding. University of Southampton, Doctoral Thesis.

Abstract

This thesis reports an investigation into the preparation and use of immobilised pyridine-2,6-dicarboxamide pincers for applications including heterogeneous catalysis, metal-ion sequestering and chiral separation.  Prior to the exploration of solid-phase techniques, a number of novel pincer-like model compounds based on bis-(4-substittued) pyridine-2,6-dicarboxamides were synthesised and their molecular and metal-ion binding properties investigated.  Crystallography was used to probe their behaviour in the solid state and UV-visible titrations were performed in order to investigate the formation of metal-ion complexes in solution.  The model compounds also formed the basis of the solid-phase aspect of this work.  Several different routes towards the immobilisation of the pyridine-cored pincers on polystyrene resin supports were investigated. Two strategies were found to be particularly useful: (i) using an ether-based linkage for linking 4-hydroxy-substittued pincers to Merrifield resin; and (ii) using a secondary amine linkage for linking 4-chloro-substituted pincers with aminomethyl resin.  The search for an all-carbon linkage from resin support to pincer unfortunately proved to be unsuccessful.

The use of pincer-like ligands in catalysis is well documented in the literature and attempts were made to match some of the metal-ion pincer-complexes prepared in this study with catalytic reactions.

A number of novel esters were prepared during the course of this work and an investigation into their solid-state properties was undertaken.

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