Synthesis of polycyclic conjugated hydrocarbons containing cyclobutadienoids and investigation of their antiaromaticity
Abstract/Contents
- Abstract
- Polycyclic conjugated hydrocarbons (PCHs) containing four-membered cyclobutadienoids (CBDs) are of great fundamental and technical interest due to the antiaromaticity brought by CBD circuits. Synthetic accessibility of such molecules, however, has been challenging and limited in scope, thus hampering the exploration and understanding of such systems. In this thesis, a versatile and efficient synthetic strategy was developed to access a large variety of CBD-containing PCHs with variable carbon structures, electronics, and topologies via catalytic arene-(oxa)norbornene annulation (CANAL) from readily accessible aryl bromides and oxanorbornenes (oNBEs). This new synthetic capability opens a myriad of opportunities for systematic investigation into CBD antiaromaticity as well as the potential applications of CBD-PCHs. With this facile method, we proposed and synthesized a series of unprecedented [3]naphthylene regioisomers, and found the regioconnectivity of [3]naphthylenes strongly affects the degree of local antiaromaticity and aromaticity for the fused CBD and naphthalenoid, respectively. Further, the C-C bond activation of CBD units was demonstrated with unsubstituted V-shaped [3]naphthylene to yield helical structures. In addition, we designed and efficiently synthesized a novel CBD-containing acene analogues, dinaphthobenzo-[1,2:4,5]dicyclobutadiene (DNBDCs), with strong antiaromaticity of the CBD units. This design also features orthogonally tunable electronic properties and molecular packing, which resulted in good device performance in organic field effect transistors.
Description
| Type of resource | text |
|---|---|
| Form | electronic resource; remote; computer; online resource |
| Extent | 1 online resource. |
| Place | California |
| Place | [Stanford, California] |
| Publisher | [Stanford University] |
| Copyright date | 2019; ©2019 |
| Publication date | 2019; 2019 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Author | Jin, Zexin |
|---|---|
| Degree supervisor | Xia, Yan, 1980- |
| Thesis advisor | Xia, Yan, 1980- |
| Thesis advisor | Kool, Eric T |
| Thesis advisor | Trost, Barry M |
| Degree committee member | Kool, Eric T |
| Degree committee member | Trost, Barry M |
| Associated with | Stanford University, Department of Chemistry. |
Subjects
| Genre | Theses |
|---|---|
| Genre | Text |
Bibliographic information
| Statement of responsibility | Zexin Jin. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis Ph.D. Stanford University 2019. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2019 by Zexin Jin
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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