Publication Date


Advisor(s) - Committee Chair

Dr. Chad A. Snyder (Director), Dr. Bangbo, DR. Rui Zhang

Degree Program

Department of Chemistry

Degree Type

Master of Science


This thesis introduces the idea of Band Theory and how it can be used to describe a solid-state materials ability to carry an electrical charge. Next, this thesis defines what makes a material a conductor, semiconductor, or insulator. Semiconductors are attracting interest in chemistry, as well as in the manufacturing of consumer electronics, because of their ability to carry a charge, without the risk of short-circuiting like traditional conductors.1,4 Organic semiconductors, which behave differently than traditional semiconductors, are of particular interest because they offer mechanical flexibility, lowcost, simplicity, and the ability to be manufactures at low temperatures.6 Nonorganic and organic semiconductors can be enhanced by a process called doping, which is further explained within this thesis. This thesis will focus on the unique properties and advantages that heterocycles, particularly thiophene and thiophene derivative complexes, and cyclopenta[c]thiophenes offer in the manufacturing of organic semiconductors. One area of thiophene research that has showed promise in leading to mass production of semiconductors derived from thiophene complexes is the use of thiophenes with electron withdrawing groups attached to the two and five position.26-27 In a recent publication in the Journal of Sulfur Chemistry a novel approach for developing thiophene derivatives was successfully investigated.27-31 This novel approach will be explained, and a successful synthetic route using 2,5-dimethylthiophene as a starting material will be

provided. This thesis also explored using 2,5-dichlorothiophene and 2,5- dibromothiophene as novel starting materials in the previously successful route utilizing 2,5-dimethylthiophene. Unfortunately, however, this area of research was unsuccessful; therefore, research shifted towards the development of the lactone 1,3-Dimethyl-7,8- dihydro-4H-thieno[3,4-c]oxepin-6-one, which is one of the many products needed for the newly proposed synthetic route of manufacturing cyclopenta[c]thiophenes utilizing a much shorter route than previously attempted. Even more importantly, the synthetic route that was attempted is filled with mostly fundamental bedrock organic chemistry that can be pulled straight from a textbook. Research stopped at the lactone due to time constraints; however, this creates an opportunity for ongoing research for future undergraduate and graduate students.


Chemistry | Organic Chemistry