Bilateral aromatic extension of corannulene nucleus
Herein we show that a dibromo imide derivative of corannulene could be subjected to a palladium-catalyzed Heck reaction in order to install aryl vinylene groups in a bilateral fashion on the C5-symmetric aromatic nucleus. A photochemically-induced oxidative cyclization then affords π-extended struct...
Saved in:
| Main Authors: | , , , |
|---|---|
| 其他作者: | |
| 格式: | Article |
| 語言: | English |
| 出版: |
2022
|
| 主題: | |
| 在線閱讀: | https://hdl.handle.net/10356/162457 |
| 標簽: |
添加標簽
沒有標簽, 成為第一個標記此記錄!
|
| 機構: | Nanyang Technological University |
| 語言: | English |
| 總結: | Herein we show that a dibromo imide derivative of corannulene could be subjected to a palladium-catalyzed Heck reaction in order to install aryl vinylene groups in a bilateral fashion on the C5-symmetric aromatic nucleus. A photochemically-induced oxidative cyclization then affords π-extended structures in isolated overall yields of 35–44 %. Due to the aromatic area extension and the presence of electron withdrawing groups, the synthesized molecules exhibit an anodic shift of ≈1 V in their first reduction potential as compared to pristine corannulene. The bilateral growth of the aromatic scaffold, therefore, represents a viable strategy to prepare π-extended corannulenes with an electron deficient character. |
|---|