The Synthesis of Room-Temperature Ionic Liquids and Their Metathesis Reactions with Dilithium Phthalocyanine
William Feld (Advisor), Eric Fossum (Committee Member), Vladomir Katovic (Committee Member)
Master of Science (MS)
A series of alkoxyalkylammonium salts has been synthesized for use in metathesis reactions with dilithium phthalocyanine. The salts, which were ionic liquids at or near room temperature, were synthesized by a nucleophilic substitution of tris[2-(2-methoxyethoxy)ethyl]amine and iodomethane, iodoethane, bromoethane, 1-bromo-propane, 1-bromo-2-(2-methoxyethoxy)ethane, and [2-[2-(2-methoxyethoxy)ethoxy]-ethoxy] p-toluenesulfonate in yields ranging from 67% - 88%. The methyl, ethyl, propyl and tetra[2-(2-methoxyethoxy)ethyl]ammonium salts were obtained for use in metathesis reactions. The salts were liquid at room temperature, with the exception of tetra[2-(2-methoxyethoxy)ethyl]ammonium bromide which was found to melt at 46° and were thermally stable to approximately 200°. The four salts were used in metathesis reactions with dilithium phthalocyanine to produce an alkoxyalkylammonium cation lithium phthalocyanine anion complex in yields from 43% - 73%. The complex products were found to be thermally stable to approximately 300° with melting temperatures ranging from 118° - 160°. The structures of tris[2-(2-methoxyethoxy)ethyl]methylammonium lithium phthalocyanine, tris[2-(2-methoxyethoxy)ethyl]propylammonium lithium phthalocyanine, and tetra[2-(2-methoxyethoxy)ethyl]ammonium lithium phthalocyanine were determined by single crystal x-ray diffraction experiments.
Department or Program
Department of Chemistry
Year Degree Awarded
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