William Feld (Advisor), Eric Fossum (Committee Member), Kenneth Turnbull (Committee Member)
Master of Science (MS)
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).
Department or Program
Department of Chemistry
Year Degree Awarded
Copyright 2011, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.