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...
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| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
| Published: |
2022
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/162457 |
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| Institution: | Nanyang Technological University |
| Language: | English |
| Summary: | 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. |
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