Publication Date
2011
Document Type
Thesis
Committee Members
William Feld (Advisor), David Grossie (Committee Member), Kenneth Turnbull (Committee Member)
Degree Name
Master of Science (MS)
Abstract
The compound 2,5-di(ethoxycarbonyl)-3,4-di(2-fluorophenyl)cyclopentadienone was successfully synthesized and led to the synthesis of terephthalates, di(hydroxymethyl)s, di(chloromethyl)s, diacids, diacid chlorides and indenofluorenediones having the pendent groups null, hexyl and 2-(4-benzothiazolyl)phenyl. All new compounds were characterized by melting point, IR, 1H NMR, 13C NMR, 19F NMR, GC/MS and combustion analysis. Most of the forementioned compounds showed an indication of restricted rotation with the appearance of trans and cis diastereomers. The asymmetric compounds showed the occurrence of four isomers. In some spectra, signals corresponding to all four isomers were visible. Through-space 1H-19F, 13C-19F and 19F-19F coupling was observed for most compounds in 1H NMR, 13C NMR and 19F NMR spectra. Polymerization of poly(2,3-bis(2-fluorophenyl)-5-hexyl-p-phenylene vinylene (BFP6-PPV) and poly(2,3-bis(2-fluorophenyl)-p-phenylene vinylene (BFP-PPV) were successful and the polymers were characterized by TGA, DSC and GPC. From GPC data, the addition of 4-tert-butylbenzyl chloride in the polymerization of BFP6-PPV appears to be ineffective in varying the molecular weights.
Page Count
265
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.
