Publication Date
2011
Document Type
Thesis
Committee Members
William Feld (Advisor), Eric Fossum (Committee Member), Kenneth Turnbull (Committee Member)
Degree Name
Master of Science (MS)
Abstract
A series of alkoxy, phenylated terephthalates has been synthesized as monomer precursors to the corresponding poly(phenylene vinylene)s (PPV). The hydroxy, phenylated terephthalate was synthesized via: 1) a Diels-Alder cycloaddition between an ethynyl boronic ester and a cyclopentadienone (CPD) with subsequent hydrolysis/oxidation of the boronate ester or 2) a Diels-Alder cycloaddition between vinylene carbonate and CPD followed by thermolysis of the bridged adduct. The hydroxy, phenylated terephthalate was alkylated via a phase-transfer reaction with iodomethane, propargyl bromide, benzyl chloride, allyl bromide, and bromobutane to produce the alkoxy, phenylated terephthalates in yields from 38.6- 91.1%. The alkoxyterephthlates were reduced with lithium aluminum hydride to either the corresponding 5-alkoxy- (methoxy, benzyloxy) or 5-hydroxy-1,4-di(hydroxymethyl)-3,4-diphenylbenzene (allyloxy, propargyloxy) in yields from 40.9-94.0%. The methoxy and benzyloxy-1,4-di(hydroxymethyl)-3,4-diphenylbenzenes were reacted with thionyl chloride to yield the corresponding 1,4-di(chloromethyl)-3,4-diphenylbenzenes. The polymerization of 5-methoxy-1,4-di(chloromethyl)-3,4-diphenylbenzene with t-BuOK yielded the insoluble polymer 5-methoxy-2,3-diphenyl-1,4-poly(phenylene vinylene).
Page Count
119
Department or Program
Department of Chemistry
Year Degree Awarded
2011
Copyright
Copyright 2011, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.
