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Exploration of Synthetic Routes to the Sulfoxide and Sulfone Derivatives of Benzotrithiophenes

by Hall, Tiffany M.

Abstract (Summary)
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.
Bibliographical Information:

Advisor:

School:Wright State University

School Location:USA - Ohio

Source Type:Master's Thesis

Keywords:benzotrithiophenes sulfoxide and sulfone derivatives of thermoelectrics

ISBN:

Date of Publication:01/01/2008

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