Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities
Triphenylamine[3]arenes (TPA[3]s), featuring [16]paracyclophane backbone with alternating carbon and nitrogen bridging atoms, were synthesized through a BF3 ⋅ Et2O-catalyzed cyclization reaction using triphenylamine derivatized monomers and paraformaldehyde. This molecular design yielded a series of...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2024
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| Online Access: | https://hdl.handle.net/10356/180913 |
| _version_ | 1826122728417001472 |
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| author | Fang, Wangjian Zhang, Jianyu Guo, Minjie Zhao, Yanli Sue, Andrew Chi-Hau |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Fang, Wangjian Zhang, Jianyu Guo, Minjie Zhao, Yanli Sue, Andrew Chi-Hau |
| author_sort | Fang, Wangjian |
| collection | NTU |
| description | Triphenylamine[3]arenes (TPA[3]s), featuring [16]paracyclophane backbone with alternating carbon and nitrogen bridging atoms, were synthesized through a BF3 ⋅ Et2O-catalyzed cyclization reaction using triphenylamine derivatized monomers and paraformaldehyde. This molecular design yielded a series of TPA[3] macrocycles with high efficiency, with their facile derivatizations also successfully demonstrated. On account of the strong electron-donating properties of the TPA moieties, these TPA[3]s exhibit remarkable delayed fluorescence, and possess a significant affinity for iodine. Furthermore, their inherent three-fold symmetry rendered TPA[3]s as novel building blocks for the construction of extended frameworks and molecular cages. This advancement expands the versatility of discrete macrocycles into complex architectures, enhancing their applicability across a broad spectrum of applications. |
| first_indexed | 2025-03-09T13:19:04Z |
| format | Journal Article |
| id | ntu-10356/180913 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-03-09T13:19:04Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1809132024-11-04T07:41:37Z Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities Fang, Wangjian Zhang, Jianyu Guo, Minjie Zhao, Yanli Sue, Andrew Chi-Hau School of Chemistry, Chemical Engineering and Biotechnology Chemistry Iodine adsorption Macrocycle Triphenylamine[3]arenes (TPA[3]s), featuring [16]paracyclophane backbone with alternating carbon and nitrogen bridging atoms, were synthesized through a BF3 ⋅ Et2O-catalyzed cyclization reaction using triphenylamine derivatized monomers and paraformaldehyde. This molecular design yielded a series of TPA[3] macrocycles with high efficiency, with their facile derivatizations also successfully demonstrated. On account of the strong electron-donating properties of the TPA moieties, these TPA[3]s exhibit remarkable delayed fluorescence, and possess a significant affinity for iodine. Furthermore, their inherent three-fold symmetry rendered TPA[3]s as novel building blocks for the construction of extended frameworks and molecular cages. This advancement expands the versatility of discrete macrocycles into complex architectures, enhancing their applicability across a broad spectrum of applications. A.C.-H.S. acknowledges the financial support from the National Science Foundation of China (grant no. 22371241) and the Starry Night Science Fund of Zhejiang University Shanghai Institute for Advanced Study (grant no. SN-ZJU-SIAS-006). J.Z. acknowledges the financial support from the National Science Foundation of China (grant no. 21927814). W.F. acknowledges the financial support from China Scholarship Council (CSC No. 202306250130) for the joint PhD program at Nanyang Technological University, Singapore. 2024-11-04T07:41:36Z 2024-11-04T07:41:36Z 2024 Journal Article Fang, W., Zhang, J., Guo, M., Zhao, Y. & Sue, A. C. (2024). Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities. Angewandte Chemie International Edition, 63(33), e202409120-. https://dx.doi.org/10.1002/anie.202409120 1433-7851 https://hdl.handle.net/10356/180913 10.1002/anie.202409120 38770884 2-s2.0-85197376523 33 63 e202409120 en Angewandte Chemie International Edition © 2024 Wiley-VCH GmbH. All rights reserved. |
| spellingShingle | Chemistry Iodine adsorption Macrocycle Fang, Wangjian Zhang, Jianyu Guo, Minjie Zhao, Yanli Sue, Andrew Chi-Hau Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities |
| title | Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities |
| title_full | Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities |
| title_fullStr | Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities |
| title_full_unstemmed | Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities |
| title_short | Triphenylamine[3]arenes: streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities |
| title_sort | triphenylamine 3 arenes streamlining synthesis of a versatile macrocyclic platform for supramolecular architectures and functionalities |
| topic | Chemistry Iodine adsorption Macrocycle |
| url | https://hdl.handle.net/10356/180913 |
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