UBC Theses and Dissertations

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UBC Theses and Dissertations

The synthesis of organoiron complexes and coordination polymers containing functionalized terpyridines Pilfold, Jessica Lori


Organic terpyridine derivatives were prepared via nucleophilic substitution at the 4′-position and coordinated with iron, ruthenium, or nickel to form several chelated complexes. These chelated compounds were reacted with chloro-terminated organoiron carboxylic acid complexes to afford terpyridine-based monomers containing three metal centres. A monomer containing a cationic iron complex with two terminal terpyridine moieties was synthesized by employing a Steglich esterification between a dicarboxylic acid organoiron complex and a hexanediol-functionalized terpyridine. The monomers containing multimetal centres were polymerized through nucleophilic aromatic substitution reactions with bisphenol A or hydroquinone, while the monomer containing one organoiron moiety and terminal terpyridine groups was polymerized through chelation to iron or nickel. The thermal properties of the polymers were investigated, with differential scanning calorimetry providing glass transition temperatures of approximately -21 °C for the iron-chelated polymers. Thermogravimetric analysis showed stepwise degradation of the cationic iron moieties, followed by the aromatic backbone, with the final decomposition step representing the loss of the bonding interaction between the iron centre and the nitrogen atoms of the chelated terpyridine groups.

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