Publication Date

2008

Document Type

Thesis

Committee Members

David Dolson (Committee Member), Eric Fossum (Advisor), Kenneth Turnbull (Committee Member)

Degree Name

Master of Science (MS)

Abstract

The synthesis of new organic materials that have the potential to be utilized in a thermoelectric application are in demand because they are able to convert thermal energy directly into electrical energy. The "end-on" sulfoxide and sulfone derivatives of Benzo[1,2-c:3,4-c':5,6-c'']trithiophene 1 were synthesized for this reason. The "end-on" mode sulfoxide derivative 13 of Benzo[1,2-c:3,4-c':5,6-c'']trithiophene 1 was prepared by utilizing 3-Carboxypyridinium Chlorochromate (CPCC) 16 and AlCl3, as an oxidizing system. The 1H NMR (DMSO-d6) spectrum displayed a singlet peak at 5.03 ppm, and the IR spectrum displayed an absorption at 1059.33cm-1, which confirmed its structure. The "end-on" mode sulfone derivative 14 was completed by a two step process: 1) oxidation of Benzo[1,2-c:3,4-c':5,6-c''] tris-(tetrahydrothiophene) 5 followed by 2) aromatization using DDQ in chlorobenzene. Verification of the compound's structure was achieved via its 1H NMR (DMSO-d6) spectrum that displayed a single peak at 6.5 ppm, which is in close approximation to the 6.64 ppm estimation.

Page Count

94

Department or Program

Department of Chemistry

Year Degree Awarded

2008

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