Calix[4]arene modified carbon electrodes as a route to asymmetric electrochemical synthesis

Buttress, James Peter (2016) Calix[4]arene modified carbon electrodes as a route to asymmetric electrochemical synthesis. Doctoral thesis, University of East Anglia.

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Abstract

This thesis explores a route towards the enantioselective electrochemical reduction of prochiral starting materials using glassy carbon electrodes modified with chiral calix[4]arenes. The research is divided into three chapters:
The first chapter discusses the synthesis of novel double-sided, “Janus” calix[4]arenes that have four molecular tethering sites. These allowed for the immobilisation of the macrocycle onto the electrode surface by either the upper or lower rim; whilst the opposite face of the calix[4]arene was appropriately functionalised to facilitate its decoration with a wide array of substrates.
The second chapter examines the immobilisation process required to fix the calix[4]arenes onto the electrode surface and the subsequent characterisation of these modified materials by both electrochemical and X-ray photoelectron spectroscopy analysis. This section also demonstrates the ease by which these functionalised materials can be further customised whilst immobilised onto the electrode surface.
The third and final part of this thesis describes attempts to use these tailored electrodes for the electrochemical reduction of prochiral ketones and compares these results to those obtained using unmodified surfaces.

Item Type: Thesis (Doctoral)
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Jackie Webb
Date Deposited: 07 Feb 2017 14:16
Last Modified: 07 Feb 2017 14:16
URI: https://ueaeprints.uea.ac.uk/id/eprint/62347
DOI:

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