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...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/162457 |
| _version_ | 1826110677473820672 |
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| author | Halilovic, Dzeneta Csókás, Dániel Webster, Richard David Stuparu, Mihaiela Corina |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Halilovic, Dzeneta Csókás, Dániel Webster, Richard David Stuparu, Mihaiela Corina |
| author_sort | Halilovic, Dzeneta |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T02:38:07Z |
| format | Journal Article |
| id | ntu-10356/162457 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T02:38:07Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1624572022-10-19T08:23:14Z Bilateral aromatic extension of corannulene nucleus Halilovic, Dzeneta Csókás, Dániel Webster, Richard David Stuparu, Mihaiela Corina School of Physical and Mathematical Sciences Science::Chemistry Corannulene Electron-Deficient Compounds 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. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) Nanyang Technological University Financial support from the Ministry of Education Singapore under the AcRF Tier 1 (2018-T1-001-176, M4012047), Agency for Science, Technology and Research, (A*STAR)-AMEIRG A1883c0006, and NTU (M4081566) is gratefully acknowledged. 2022-10-19T08:23:14Z 2022-10-19T08:23:14Z 2022 Journal Article Halilovic, D., Csókás, D., Webster, R. D. & Stuparu, M. C. (2022). Bilateral aromatic extension of corannulene nucleus. European Journal of Organic Chemistry, 2022(18), e202101548-. https://dx.doi.org/10.1002/ejoc.202101548 1434-193X https://hdl.handle.net/10356/162457 10.1002/ejoc.202101548 2-s2.0-85125228854 18 2022 e202101548 en 2018-T1-001-176 M4012047 A1883c0006 M4081566 European Journal of Organic Chemistry © 2022 Wiley-VCH GmbH. All rights reserved. |
| spellingShingle | Science::Chemistry Corannulene Electron-Deficient Compounds Halilovic, Dzeneta Csókás, Dániel Webster, Richard David Stuparu, Mihaiela Corina Bilateral aromatic extension of corannulene nucleus |
| title | Bilateral aromatic extension of corannulene nucleus |
| title_full | Bilateral aromatic extension of corannulene nucleus |
| title_fullStr | Bilateral aromatic extension of corannulene nucleus |
| title_full_unstemmed | Bilateral aromatic extension of corannulene nucleus |
| title_short | Bilateral aromatic extension of corannulene nucleus |
| title_sort | bilateral aromatic extension of corannulene nucleus |
| topic | Science::Chemistry Corannulene Electron-Deficient Compounds |
| url | https://hdl.handle.net/10356/162457 |
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