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Title: The synthesis and photophysical properties of novel phthalocyanines for potential application in photodynamic therapy.
Author: Burton, Anthony.
Awarding Body: University of East Anglia
Current Institution: University of East Anglia
Date of Award: 1999
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Phthalocyanines are a group of molecules, which have been studied extensively due partly to their use and potential in a wide variety of applications, but also on account of the seemingly endless list of differently substituted moieties, which in principle may be prepared. The history of the compounds in general are discussed briefly in Chapter 1 of this thesis, while Chapter 2 focuses on Photodynamic Therapy, an area in which they have more recently been found to exhibit excellent potential. The synthesiso of novel phthalocyanines for potential application in PDT is reported in Chapter 3. The current research investigated the synthesis of binuclear Pcs from the linking of two preformed phthalocyanine rings by means of an oxalyl bridge functionality and also from the mixed cyclisation of phthalonitriles with bisphthalonitriles, which proved to be extremely problematic. The synthesis of water-soluble phthalocyanine derivatives was investigated as a sideline, which resulted in the synthesis of a novel phthalocyanine monomer substituted with eight triethylene glycol chains. Efforts to synthesise a phthalocyanine linked to a glucose unit were unsuccessful. Chapter 4 describes research into the photophysical properties of a number of mononuclear and binuclear phthalocyanines synthesised both in the current work and also compounds synthesised by co-workers. The electronic absorption and fluorescence spectra of the compounds are investigated, and the absorption spectrum of a purely cofacial dimeric structure is obtained by calculation from the spectrum of one of the binuclear derivatives. Laser Flash Photolysis was performed on a number of the samples, determining triplet lifetimes, triplet quantum yields and singlet oxygen quantum yields. The effect of aggregation on the photoproperties of phthalocyaninesis investigated in Chapter 5. The current work involved low temperature absorption and fluorescence spectroscopy on a number of mononuclear and binuclear phthalocyanine derivatives. The nature of the aggregated structures, which were observed to form at 77K, are then rationalised with reference to previous research into phthalocyanine aggregates and crystal structures.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Photosensitisers; Binuclear; PDT; Aggregation Chemistry, Organic Medicine