Date of Award

1992

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Mark L. McLaughlin

Abstract

The goal of this research was to synthesize conductive polymers based on repeating ferrocene units. During the course of this study, the design of the conductive polymers evolved from the initial model based on "stacked" ferrocenes where ethano bridged cyclopentadienyl rings are linked by iron(II), to the latest ferrocene-diene model where ferrocene units were linked by double bonds. In the pursuit of these elusive monomers, attempts at their synthesis led down dead-end routes, even though new molecules were synthesized. Some of these dead-ends proved productive as in the synthesis of chiral titanocene derivatives. All the work reported in this dissertation had the eventual goal of synthesizing potential monomers for ferrocene conducive polymers. This dissertation is divided into three chapters. Chapter one describes the attempted synthesis of thiophene derivatives where a cyclopentadienyl ring is fused to the (c) -face. Although the target molecule was never synthesized, a convenient and safe new synthesis of 3,4-dibromo-2,5-dimethyl thiophene was developed along with the synthesis and full characterization of 3-bromo-4-trimethylsilyl-2,5-dimethylthiophene. Chapter two describes the design of asymmetric hydrogenation catalysts and the convenient synthesis of chiral titanocene derivatives. Chapter three summarizes the history of our attempts to prepare ferrocene containing conductive polymers and describes the synthesis of ferrocenophenes and diethano bridged bis(cyclopentadienyl) compounds for use as monomeric precursors to conductive polymers based on repeating ferrocene units.

Pages

174

DOI

10.31390/gradschool_disstheses.5431

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