Synthesis and investigation of novel material and medicinal phthalocyanine compounds.
Becauseo f the importance of phthalocyaninesa s functional materials and
in medicine their synthesis and applications have been well documented in the
literature. In the introductory chapter (chapter 1) a brief account of preparative
methods and applications is outlined.
Photodynamic therapy (PDT) is becoming a widely investigated area of
research. Phthalocyanine drug candidates for PDT have received a great deal of
interest. Novel aromatic, heteroaromatic and functionalised aromatic asymmetric
3: 1 phthalocyaninesw ere synthesisede, xploiting the Suzuki cross-coupling
reaction. Systematic investigation into their possible use as PDT candidates was
explored in chapter 2.
As a result of unexpected interactions between pyridyl functionalised 3: 1
zinc phthalocyanines, further investigation into complexes of `edge-to-face'
assembliesw as undertaken.T he synthesiso f these assembliesth rough Lewis
acid/base interactions between the nitrogen lone pair and a metal centre has been
investigatedb y 'H NMR spectroscopy.A pplication to both phthalocyaninea nd
phthalonitrile compounds produced some interesting `supramolecular' assemblies.
Finally, to further exploit these interactions a photoswitchable, selfassembledm
onolayer wasp repared.T he monolayerw as designedt o isomerise
under irradiation with light, to facilitate an `on-off type switch, that could bind a
metal centred phthalocyanine.