Pyrene-containing twistarene : twelve benzene rings fused in a row
Success in obtaining higher-order twistarenes with precise structures is very important for fundamentally understanding the relationship between the structures and physical properties/optoelectronic applications. In this research, by using the advantages from a retro-Diels-Alder process (clean react...
| Main Authors: | , , , , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/144117 |
| _version_ | 1826121203968901120 |
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| author | Chen, Wangqiao Li, Xinxiong Long, Guankui Li, Yongxin Ganguly, Rakesh Zhang, Mingtao Aratani, Naoki Yamada, Hiroko Liu, Ming Zhang, Qichun |
| author2 | School of Materials Science and Engineering |
| author_facet | School of Materials Science and Engineering Chen, Wangqiao Li, Xinxiong Long, Guankui Li, Yongxin Ganguly, Rakesh Zhang, Mingtao Aratani, Naoki Yamada, Hiroko Liu, Ming Zhang, Qichun |
| author_sort | Chen, Wangqiao |
| collection | NTU |
| description | Success in obtaining higher-order twistarenes with precise structures is very important for fundamentally understanding the relationship between the structures and physical properties/optoelectronic applications. In this research, by using the advantages from a retro-Diels-Alder process (clean reaction) and the cross-conjugated nature of the pyrene unit, a novel dodeca-twistarene was prepared for the first time. Its structure, confirmed by single-crystal XRD analysis, indicates that it possesses a twisted angle (≈30°), and two neighboring molecules in the crystal lattice are perpendicular to each other because of the twisted character and the strong intermolecular CH-π interactions. However, its basic physicochemical properties suggest its instability in air derives from its elevated HOMO energy level, although NICS calculations confirm that the pyrene units contribution poorly to the π conjugation of the overall molecule. |
| first_indexed | 2024-10-01T05:28:53Z |
| format | Journal Article |
| id | ntu-10356/144117 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:28:53Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1441172023-07-14T15:54:15Z Pyrene-containing twistarene : twelve benzene rings fused in a row Chen, Wangqiao Li, Xinxiong Long, Guankui Li, Yongxin Ganguly, Rakesh Zhang, Mingtao Aratani, Naoki Yamada, Hiroko Liu, Ming Zhang, Qichun School of Materials Science and Engineering Computational Center for Molecular Science, College of Chemistry, Nankai University. Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST). Engineering::Materials dodecatwistarcene CH–π interactions Success in obtaining higher-order twistarenes with precise structures is very important for fundamentally understanding the relationship between the structures and physical properties/optoelectronic applications. In this research, by using the advantages from a retro-Diels-Alder process (clean reaction) and the cross-conjugated nature of the pyrene unit, a novel dodeca-twistarene was prepared for the first time. Its structure, confirmed by single-crystal XRD analysis, indicates that it possesses a twisted angle (≈30°), and two neighboring molecules in the crystal lattice are perpendicular to each other because of the twisted character and the strong intermolecular CH-π interactions. However, its basic physicochemical properties suggest its instability in air derives from its elevated HOMO energy level, although NICS calculations confirm that the pyrene units contribution poorly to the π conjugation of the overall molecule. Ministry of Education (MOE) Accepted version Q.Z acknowledges financial support from AcRF Tier 1 (RG 111/17, RG 2/17, RG 114/16, RG 8/16) and Tier 2 (MOE 2017- T2-1-021), Singapore. Dr. Liu acknowledges funding support from M4062018. 2020-10-14T02:28:25Z 2020-10-14T02:28:25Z 2018 Journal Article Chen, W., Li, X., Long, G., Li, Y., Ganguly, R., Zhang, M., ... Zhang, Q. (2018). Pyrene-containing twistarene : twelve benzene rings fused in a row. Angewandte Chemie International Edition, 57(41), 13555-13559. doi:10.1002/anie.201808779 1521-3773 https://hdl.handle.net/10356/144117 10.1002/anie.201808779 30144255 41 57 13555 13559 en AcRF Tier 1 RG 111/17 AcRF Tier 1 RG 2/17 AcRF Tier 1 RG 114/16 AcRF Tier w RG 8/16 MOE 2017-T2-1-021 NTU Grant M4062018 Angewandte Chemie International Edition This is the accepted version of the following article: Chen, W., Li, X., Long, G., Li, Y., Ganguly, R., Zhang, M., ... Zhang, Q. (2018). Pyrene-containing twistarene : twelve benzene rings fused in a row. Angewandte Chemie International Edition, 57(41), 13555-13559. doi:10.1002/anie.201808779, which has been published in final form at 10.1002/anie.201808779. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy [https://authorservices.wiley.com/authorresources/Journal-Authors/licensing/self-archiving.html]. application/pdf |
| spellingShingle | Engineering::Materials dodecatwistarcene CH–π interactions Chen, Wangqiao Li, Xinxiong Long, Guankui Li, Yongxin Ganguly, Rakesh Zhang, Mingtao Aratani, Naoki Yamada, Hiroko Liu, Ming Zhang, Qichun Pyrene-containing twistarene : twelve benzene rings fused in a row |
| title | Pyrene-containing twistarene : twelve benzene rings fused in a row |
| title_full | Pyrene-containing twistarene : twelve benzene rings fused in a row |
| title_fullStr | Pyrene-containing twistarene : twelve benzene rings fused in a row |
| title_full_unstemmed | Pyrene-containing twistarene : twelve benzene rings fused in a row |
| title_short | Pyrene-containing twistarene : twelve benzene rings fused in a row |
| title_sort | pyrene containing twistarene twelve benzene rings fused in a row |
| topic | Engineering::Materials dodecatwistarcene CH–π interactions |
| url | https://hdl.handle.net/10356/144117 |
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