Towards the synthesis of novel phthalocyanine derivatives for PDT and and near-infrared absorbing dyes
The phthalocyanines are a family of intensely coloured compounds (usually blue or
green) which are structurally similar to the porphyrins. A brief summary of different
phthalocyanines reported in the literature so far, their preparations and applications are
detailed in the introductory chapter.
A number of substituted phthalocyanines are already known as effective
photosensitisers for photodynamic therapy (PDT). Therefore the design and synthesis of
a series of new unsymmetrically substituted phthalocyanine derivatives has been
described. Also the preparation of a series of phthalocyanines bearing one or more 4-
tert-butylphenyl substituents was investigated. Reports in the literature suggested such
derivatives should be able to bind to cyclodextrins to afford water soluble formulations.
The synthesis of highly soluble axially substituted phthalocyanine derivatives
containing indium within the macrocycle cavity is described. These materials have been
found to have useful optical and electrical properties. One compound of this series is
chiral and its solid state structure has been determined by X-ray diffraction analysis.
The synthesis of metallated and non-metallated porphyrazines has been explored. The
metal-free derivative generates conventional "face-to-face" assemblies in solution,
whereas the zinc analogue forms alternative "edge-to-face" complexes via axial
ligation. Finally, the research described in the fourth chapter involves the synthesis of
new alkylsulfanyl and arylsulfanyl phthalocyanine derivatives. The complexation of
such materials with silver(I) ion has been investigated and monitored by UV/vis