William Feld (Advisor), Eric Fossum (Committee Member), David Grossie (Committee Member)
Master of Science (MS)
The alkyne 1-(benzyloxy)-4-(propargyloxy)benzene was reacted with 2,5-di(carboethoxy)3,4-diphenylcyclopentadienone to yield diethyl 5-((4-(benzyloxy)phenoxy)methyl)-2,3-diphenylterephthalate. The terephthalate was reduced with lithium aluminum hydride to produce 5-((4-(benzyloxy)phenoxy)methyl)-1,4-di(hydroxymethyl)-2,3-diphenylbenzene. The diol was reacted with thionyl chloride to yield the monomer 5-((4-(benzyloxy)phenoxy)methyl)-1,4-di(chloromethyl)-2,3-diphenylbenzene that has a pendent protected phenol function. The new compounds were characterized by melting point, IR, 1H NMR, 13C NMR spectroscopy and elemental analysis. Polymerization of the dichloro monomer via a Gilch polymerization yielded poly[(2,3-diphenyl-(5-((4-(benzyloxy)phenoxy)methyl)-1,4-phenylene) vinylene]. The polymer was characterized by IR, 1H NMR spectroscopy, TGA and DSC. The polymer was insoluble in most solvents but partially soluble in chlorinated solvents. The solid polymer fluoresced a bluish-green under UV light either in solution or in the solid state.
Department or Program
Department of Chemistry
Year Degree Awarded
Copyright 2013, some rights reserved. My ETD may be copied and distributed only for non-commercial purposes and may not be modified. All use must give me credit as the original author.
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.