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    Synthesis and polymerization of supramolecular assemblies of octasubstituted phthalocyanines

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    Author
    Drager, Anthony Steven
    Issue Date
    2001
    Keywords
    Chemistry, Organic.
    Chemistry, Polymer.
    Engineering, Materials Science.
    Advisor
    O'Brien, David F.
    
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    Show full item record
    Publisher
    The University of Arizona.
    Rights
    Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
    Abstract
    Substituted phthalocyanines (Pc's) are an important class of organic molecules, which have shown promise in the field of organo-electronics. The goal of the current research was to synthesize a new class of polymerizable Pc's. It was hoped that the new class of compounds would exhibit similar liquid crystalline and self organization properties that had been demonstrated by 2,3,9,10,16,17,23,24-octakis(2-benzyoxyethoxy) phthalocyanine. This Pc formed stable Langmuir monolayer and bilayers, which could be transferred to solid supports without losing the long-range order. The initial reactive Pc was 2,3,9,10,16,17,23,24-octakis(2-benzyoxyethoxy) phthalocyanine. The monomer was a beta-substituted styrene that was located within the alkoxy chains, to prevent inter-columnar cross-linking. The styrene functionalities were dimerized (35% reaction) by photolysis at 254 nm to form cyclo-butanes. The rod-like polymers were characterized using AFM and MALDI-TOF mass spectral analysis and the molecular rods obtained had a mean length of 72 nm. The styrylethoxy Pc was shown to be more crystalline then the previous benzyloxyethoxy Pc's, in order to correct this a new class of reactive Pc's were developed that contained a second oxygen atom. DSC data on the cinnamyloxyethoxy Pc shows that the lower temperature for the liquid crystalline mesophase was restored. Polymerization experiments performed on the cinnamyloxyethoxy Pc showed faster and 2x higher percent conversion. The research detailed in this dissertation describes a novel Diels-Alder synthetic approach to this important class of molecules and a new generic route to polymer rods of Pc.
    Type
    text
    Dissertation-Reproduction (electronic)
    Degree Name
    Ph.D.
    Degree Level
    doctoral
    Degree Program
    Graduate College
    Chemistry
    Degree Grantor
    University of Arizona
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