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

Hall, Tiffany M.
http://rave.ohiolink.edu/etdc/view?acc_num=wright1220816774

Abstract Details

2008, Master of Science (MS), Wright State University, Chemistry.
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.
Eric Fossum, PhD (Advisor)
Kenneth Turnbull, PhD (Committee Member)
David Dolson, PhD (Committee Member)
94 p.
Chemistry
benzotrithiophenes; sulfoxide and sulfone derivatives of benzotrithiophenes, thermoelectrics

Recommended Citations

Citations

  • Hall, T. M. (2008). Exploration of Synthetic Routes to the Sulfoxide and Sulfone Derivatives of Benzotrithiophenes [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1220816774

    APA Style (7th edition)

  • Hall, Tiffany. Exploration of Synthetic Routes to the Sulfoxide and Sulfone Derivatives of Benzotrithiophenes. 2008. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1220816774.

    MLA Style (8th edition)

  • Hall, Tiffany. "Exploration of Synthetic Routes to the Sulfoxide and Sulfone Derivatives of Benzotrithiophenes." Master's thesis, Wright State University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=wright1220816774

    Chicago Manual of Style (17th edition)

wright1220816774
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© 2008, all rights reserved.
This open access ETD is published by Wright State University and OhioLINK.