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Title: An investigation into the synthesis of potentially chemiluminescent novel molecules
Author: Rudge, J. B.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 2005
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Chemiluminescent compounds are essential tools as probes for the analysis of biological molecules. One such family, the Acridinium Esters, are safe to use and more sensitive than radio labels. The chemistry of the light-emitting reaction of the acridinium esters is a simple hydroperoxidation in basic conditions. However, like all chemiluminescent systems, the light-emitting reaction and chemical stability of these molecules can be vastly improved. Chapter Two explores the chemistry around synthesising a sulfonate ester derivative of the standard ester (i.e. a carboxylate). From molecular modelling studies, it was predicted that sulfonate esters would react more energetically during hydroperoxidation. However, synthesis of 9-substitued acridinium sulfonate esters was impossible to achieve. Methods for esterification resulted in substitution of the sulfonate for a nucleophile, such as HO- or Cl-. Moreover, the sulfonate anion was proven to be a very poor nucleophile, thus direct attack of the sulfonate ligand onto a nucleophile such as methyl iodide, was found to be unfavourable. Chapter Three explores the synthesis of a novel group potentially chemiluminescent molecules based on the original acridinium ester design but substituting the acridine ring for a pyridine ring. It was hoped through inter or intramolecular energy transfer to a bound fluor, that light of a desired wavelength could be selected based on choice of fluor. Finally, chapter four describes the synthesis of a family of molecules based on the parent molecule acridine-9-carboxylic acid pyridine-2-ylamide. Although classically, acridinium amides have proven to be too unreactive on hydroperoxidation, it was hoped that as the pyridine ring is electron withdrawing that it would improve said reactivity. However, when methylating these esters to potentially form an N-methyl acridinium, methylation preferentially occurred on the pyridine ring.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available