Synthesis and properties of azahomocorannulenyl cations and radicals
Cycloheptatrienyl (tropyl) molecules are representative non-alternant hydrocarbons that offer interesting chemistry because of their unique structures and properties. However, there have been a limited number of polycyclic aromatic tropyl cations and radicals reported in the literature. Herein, we r...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/176107 |
| _version_ | 1826115884832260096 |
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| author | Hamamoto, Yosuke Ochiai, Kotaro Li, Yongxin Tapavicza, Enrico Ito, Shingo |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Hamamoto, Yosuke Ochiai, Kotaro Li, Yongxin Tapavicza, Enrico Ito, Shingo |
| author_sort | Hamamoto, Yosuke |
| collection | NTU |
| description | Cycloheptatrienyl (tropyl) molecules are representative non-alternant hydrocarbons that offer interesting chemistry because of their unique structures and properties. However, there have been a limited number of polycyclic aromatic tropyl cations and radicals reported in the literature. Herein, we report the synthesis of a series of azahomocorannulene derivatives, where the key reactions are a 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with dibenzotropone and a subsequent palladium-catalyzed cyclization. X-ray diffraction analysis revealed that the obtained azahomocorannulenyl cation and radical adopt planar structures and exhibit unique packing structures. Their electronic and optical properties were investigated experimentally and theoretically to reveal their aromatic character. |
| first_indexed | 2024-10-01T04:02:25Z |
| format | Journal Article |
| id | ntu-10356/176107 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:02:25Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1761072024-05-13T07:20:15Z Synthesis and properties of azahomocorannulenyl cations and radicals Hamamoto, Yosuke Ochiai, Kotaro Li, Yongxin Tapavicza, Enrico Ito, Shingo School of Chemistry, Chemical Engineering and Biotechnology Chemistry Azahomocorannulene Polycyclic aromatic molecules Cycloheptatrienyl (tropyl) molecules are representative non-alternant hydrocarbons that offer interesting chemistry because of their unique structures and properties. However, there have been a limited number of polycyclic aromatic tropyl cations and radicals reported in the literature. Herein, we report the synthesis of a series of azahomocorannulene derivatives, where the key reactions are a 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with dibenzotropone and a subsequent palladium-catalyzed cyclization. X-ray diffraction analysis revealed that the obtained azahomocorannulenyl cation and radical adopt planar structures and exhibit unique packing structures. Their electronic and optical properties were investigated experimentally and theoretically to reveal their aromatic character. Nanyang Technological University This work was supported by Nanyang Technological University. 2024-05-13T07:20:15Z 2024-05-13T07:20:15Z 2024 Journal Article Hamamoto, Y., Ochiai, K., Li, Y., Tapavicza, E. & Ito, S. (2024). Synthesis and properties of azahomocorannulenyl cations and radicals. Angewandte Chemie International Edition, 63(7), e202319022-. https://dx.doi.org/10.1002/anie.202319022 1433-7851 https://hdl.handle.net/10356/176107 10.1002/anie.202319022 38153357 2-s2.0-85182190988 7 63 e202319022 en Angewandte Chemie International Edition © 2023 Wiley-VCH GmbH. All rights reserved. |
| spellingShingle | Chemistry Azahomocorannulene Polycyclic aromatic molecules Hamamoto, Yosuke Ochiai, Kotaro Li, Yongxin Tapavicza, Enrico Ito, Shingo Synthesis and properties of azahomocorannulenyl cations and radicals |
| title | Synthesis and properties of azahomocorannulenyl cations and radicals |
| title_full | Synthesis and properties of azahomocorannulenyl cations and radicals |
| title_fullStr | Synthesis and properties of azahomocorannulenyl cations and radicals |
| title_full_unstemmed | Synthesis and properties of azahomocorannulenyl cations and radicals |
| title_short | Synthesis and properties of azahomocorannulenyl cations and radicals |
| title_sort | synthesis and properties of azahomocorannulenyl cations and radicals |
| topic | Chemistry Azahomocorannulene Polycyclic aromatic molecules |
| url | https://hdl.handle.net/10356/176107 |
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