The syntheses of phthalocyanines and particularly substituted phthalocyanines, together with some of their main applications, are described. Asymmetrically octasubstituted phthalocyanines, where the substituents on one benzene ring differ from the substituents on the other three rings are most commonly obtained from statistical mixtures of precursors derived from phthalic acid. The synthesis of a series of such compounds together with their substituted phthalonitrile precursors containing both hydrophilic and hydrophobic side-chain substituents is discussed. This novel series of nonperipherally substituted amphiphilic phthalocyanines were shown to possess liquid crystalline properties. The various liquid crystal discotic mesophases were characterised. As a consequence of their hydrophilic-hydrophobic balance and high solubility in organic solvents, the compounds were studied as Langmuir-Blodgett films. The synthesis and Langmuir monolayer behaviour of peripherally octa-t-butylphthalocyanine is also described. The latter part of this thesis includes a discussion of the mechanisms of the synthesis of phthalocyanines from various precursors and particularly from phthalonitrile, which complements the synthetic aspects of the work. The thesis concludes with an investigation into the feasibility of a stepwise conversion of phthalonitrile precursors into the macrocycle for the preparation of asymmetrically substituted phthalocyanines.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:293193 |
| Date | January 1991 |
| Creators | Chambrier, Isabelle |
| Publisher | University of East Anglia |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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