Publication Date
2012
Document Type
Thesis
Committee Members
William Feld (Advisor), Eric Fossum (Committee Member), Vladomir Katovic (Committee Member)
Degree Name
Master of Science (MS)
Abstract
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.
Page Count
102
Department or Program
Department of Chemistry
Year Degree Awarded
2012
Copyright
Copyright 2012, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.
