Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry
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University of Cincinnati / OhioLINK
2019
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| Online Access: | http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563 |
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ndltd-OhioLink-oai-etd.ohiolink.edu-ucin15635257332615632021-08-16T05:10:40Z Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry Wang, Cong Chemistry Polyaromatic hydrocarbons mechanochemistry acene silica gel rate enhancement surface charge 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. 2019-10-18 English text University of Cincinnati / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563 http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws. |
| collection |
NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Chemistry Polyaromatic hydrocarbons mechanochemistry acene silica gel rate enhancement surface charge |
| spellingShingle |
Chemistry Polyaromatic hydrocarbons mechanochemistry acene silica gel rate enhancement surface charge Wang, Cong Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry |
| author |
Wang, Cong |
| author_facet |
Wang, Cong |
| author_sort |
Wang, Cong |
| title |
Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry |
| title_short |
Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry |
| title_full |
Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry |
| title_fullStr |
Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry |
| title_full_unstemmed |
Synthesis of Polyaromatic Hydrocarbons via Mechanochemistry |
| title_sort |
synthesis of polyaromatic hydrocarbons via mechanochemistry |
| publisher |
University of Cincinnati / OhioLINK |
| publishDate |
2019 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=ucin1563525733261563 |
| work_keys_str_mv |
AT wangcong synthesisofpolyaromatichydrocarbonsviamechanochemistry |
| _version_ |
1719460071316914176 |