Polymer-supported pincers for selective molecular and ionic binding
Polymer-supported pincers for selective molecular and ionic binding
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.
University of Southampton
2005
Golden, Christopher Alex
(2005)
Polymer-supported pincers for selective molecular and ionic binding.
University of Southampton, Doctoral Thesis.
Record type:
Thesis
(Doctoral)
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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Published date: 2005
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Local EPrints ID: 465711
URI: http://eprints.soton.ac.uk/id/eprint/465711
PURE UUID: 45f7f11f-1f39-4180-9b53-2840b3136b22
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Date deposited: 05 Jul 2022 02:41
Last modified: 05 Jul 2022 02:41
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Author:
Christopher Alex Golden
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