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Publication Date

Fall 2019

Degree Type

Thesis - Campus Access Only

Degree Name

Master of Science (MS)




David J. Brook

Subject Areas

Physical chemistry; Organic chemistry


Spintronic materials use the spin of an electron to gain new functionality in electronic devices. Consequently, controlling and understanding the transport and interaction of spins in conductors is integral to their development. For organic conductors, one possible method for controlling spins involves attachment of stable free radicals to the conducting polymer chain in order to influence the spin of the conduction electrons. Previously published work has shown that verdazyl free radicals can interact strongly with attached unpaired electrons, but this interaction can be manipulated with acid/base chemistry, suggesting a potential application in this area. Expanding on this idea, we have synthesized verdazyl-substituted compounds that are models for polyaniline and determined their oxidation states through spectroscopy and spectroelectrochemical techniques. Results indicate that there are four redox states of N,N’-Bis-(1,5-diisopropyl-6-oxoverdazylphenyl)-phenylenediamine (12). Though results are not yet conclusive, it appears that compound 12 undergoes oxidation of the verdazyl first, giving a low spin state (S=1/2) at ambient temperature while at lower temperatures, oxidation of the phenylene diamine linker gives a high spin (S=3/2) tautomers. Further research will be needed to investigate a suitable efficient synthesis 12 and analogs in order to facilitate more detailed investigation.