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Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry

Wang, Cong
http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563

Abstract Details

2019, PhD, University of Cincinnati, Arts and Sciences: Chemistry.
Polyaromatic hydrocarbons (PAHs), including acene derivatives, are very promising materials and its unique properties are attractive to various industries. However, their synthesis in solution is difficult due to its low solubility and stability. Practical and solvent free synthetic methods are necessary to capitalize of their potential. Therefore, the synthesis of linear acene derivatives was studied under solvent free conditions using ball milling conditions. High speed ball milling (HSBM), as one popular technique of mechanochemistry, due to its unique properties, make itself an ideal technique for this study. HSBM is used as a grinding technique as well as a reaction container. In many cases, reactions happen without adding any solvent. This property makes it possible for us to bypass the solubility issue of PAHs and to synthesis this kind of compounds without solvent. Synthesis of linear acenes via benzyne and the Wittig reaction were investigated in this project. It was determined that benzyne was generated under solvent-free conditions, however due to the limited control of benzyne under these conditions, only small amount of desired products were obtained. Through a series of iterative reactions including the Wittig reaction, reduction and oxidation, we developed a more practical, greener and solvent free synthesis method of acenes under mechanochemical conditions. We learned that as the size of the linear acene increased the reactivity of the molecule decreased, due to high π-π stacking. Silica gel was found to be an efficient additive to break π-π stacking and can speed up some types of reactions, including IBX oxidation, Diels-Alder reaction, nucleophilic reaction, and Wittig reaction. We think the surface charge of additive is the most important reason of rate enhancement effect.
James Mack, Ph.D. (Committee Chair)
Hairong Guan, Ph.D. (Committee Member)
Anna Gudmundsdottir, Ph.D. (Committee Member)
148 p.
Chemistry
Polyaromatic hydrocarbons; mechanochemistry; acene; silica gel; rate enhancement; surface charge

Recommended Citations

Citations

  • Wang, C. (2019). Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry [Doctoral dissertation, University of Cincinnati]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563

    APA Style (7th edition)

  • Wang, Cong. Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry. 2019. University of Cincinnati, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563.

    MLA Style (8th edition)

  • Wang, Cong. "Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry." Doctoral dissertation, University of Cincinnati, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563

    Chicago Manual of Style (17th edition)

ucin1563525733261563
104
© 2019, all rights reserved.
This open access ETD is published by University of Cincinnati and OhioLINK.