Attempted synthesis of new intrinsically electroactive polymers by the condensation of cyclopentadienyl anions with diesters, 1990

Yan, Jingbo

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Title: Attempted synthesis of new intrinsically electroactive polymers by the condensation of cyclopentadienyl anions with diesters, 1990
Author: Yan, Jingbo
Decade: 1990-1999
Abstract: Treatment of diethyl oxalate with two equivalents of sodium cyclopentadienide in THF gave, upon work-up, biscyclopentadienyldiketone-THF contaminated with a small amount of cyclopentadienylethoxyldiketone in 87% yield. Treatment of diethyl oxalate with four equivalents of sodium cyclopentadienide in THF led to, upon work-up, clean biscyclopentadienyldiketone-THF in 91% yield. Treatment of diethyl oxalate with one equivalent of sodium cyclopentadienide in THF gave, upon work-up, oligomers of poly(1,3-diketocyclopentadienyl)-THF in 92% yield. Treatment of diethyl oxalate with one equivalent of Lithium cyclopentadienide in THF gave, upon work-up, oligomers of poly( 1 ,3-dicyclopentadienyl)-THF in 66% yield. Treatment of biscyclopentadienyl diketone with diethyl oxalate in H2O or THF gave, upon work-up, oligomers of poly( 1 ,3-diketocyclopentadienyl). Treatment of diethyl oxalate with sodium cyclopentadienide in the presence of triethylamine in THF gave, upon work-up, oligomers of poly(1,3-dicyclopentadienyl).THF. Treatment of cyclopentadienyl anion with diethyl carbonate in THF gave, upon work-up, oligomers of poly(ketocyclopentadienyl) in 85% yield. Treatment of diethyl carbonate with sodium cyclopentadienide in the presence of triethylamine in THF gave, upon work-up, oligomers of poly(ketocyclopentadienyl)-THF in 83% yield. Treatment of biscyclopentadienyldiketone with iron (II) chloride in H20 or THF gave, upon work-up, brown solids that are paramagnetic. Treatment of poly(1,3-dicyclopentadienyl) with iron (II) chloride in H20 gave, upon work-up, a black solid that are paramagnetic. The new materials prepared were found to be insulators at room temperature when dry and solvent free. Composites prepared from the new materials in this study with PEO and TCNQ are insulators at room temperature and exhibit conductivities at temperature above 60 C in the range of 10-5 to 10-7 S cm-1.
Document Type: text
Format: application/pdf
Date of Award: 1990-08-01
Degree Type: thesis
Degree Name: Master of Science (MS)
Granting Institution: Clark Atlanta University
Department: School of Arts and Sciences, Chemistry
Advisor: Mintz, Eric A.
Institution: Clark Atlanta University
Geographic Location: Georgia--Atlanta
Handle: http://hdl.handle.net/20.500.12322/cau.td:1990_yan_jingbo