General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activation
Abstract Poly‐substituted olefins, one of the most important aggregation‐induced emission luminogens (AIEgens), have garnered significant attention due to their various applications in chemical‐ and bio‐sensing, bio‐imaging, and opto‐electronics. However, the synthetic methods for these olefins rema...
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Wiley
2025-01-01
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| Online Access: | https://doi.org/10.1002/agt2.650 |
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| author | Bowei Ma Xinyu Liang Gu Xu Guanghao Zhang Lutang Zhao Liangzhuo Ma Wenbin Xie Xiang Li Qinqin Shi Kaikai Wen Hui Huang |
| author_facet | Bowei Ma Xinyu Liang Gu Xu Guanghao Zhang Lutang Zhao Liangzhuo Ma Wenbin Xie Xiang Li Qinqin Shi Kaikai Wen Hui Huang |
| author_sort | Bowei Ma |
| collection | DOAJ |
| description | Abstract Poly‐substituted olefins, one of the most important aggregation‐induced emission luminogens (AIEgens), have garnered significant attention due to their various applications in chemical‐ and bio‐sensing, bio‐imaging, and opto‐electronics. However, the synthetic methods for these olefins remain limited, impeding the progress of AIEgens. This study introduces an unprecedented cross‐coupling reaction between aryl sulfonium triflates and tosylhydrazones from naturally abundant thioethers and ketones. The generality of this method is exemplified by the facile synthesis of over forty poly‐substituted olefins. Importantly, the luminescent properties of these AIEgens (e.g., quantum yield and emission color) can be easily tuned by adjusting the substituents of the electrophile and nucleophile substrates, exhibiting excellent performance in bio‐imaging. Notably, the mechanistic studies reveal the critical role of β‐H elimination in the formation of the double bond. This contribution provides an efficient method to synthesize poly‐substituted olefins, pushing forward the development of AIEgens. |
| format | Article |
| id | doaj-art-78bcbf2f78754f06b12ecc7aa6d84684 |
| institution | Kabale University |
| issn | 2692-4560 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Wiley |
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| series | Aggregate |
| spelling | doaj-art-78bcbf2f78754f06b12ecc7aa6d846842025-01-21T08:57:07ZengWileyAggregate2692-45602025-01-0161n/an/a10.1002/agt2.650General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activationBowei Ma0Xinyu Liang1Gu Xu2Guanghao Zhang3Lutang Zhao4Liangzhuo Ma5Wenbin Xie6Xiang Li7Qinqin Shi8Kaikai Wen9Hui Huang10College of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaCollege of Materials Science and Opto‐Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum PhysicUniversity of Chinese Academy of SciencesBeijingP. R. ChinaAbstract Poly‐substituted olefins, one of the most important aggregation‐induced emission luminogens (AIEgens), have garnered significant attention due to their various applications in chemical‐ and bio‐sensing, bio‐imaging, and opto‐electronics. However, the synthetic methods for these olefins remain limited, impeding the progress of AIEgens. This study introduces an unprecedented cross‐coupling reaction between aryl sulfonium triflates and tosylhydrazones from naturally abundant thioethers and ketones. The generality of this method is exemplified by the facile synthesis of over forty poly‐substituted olefins. Importantly, the luminescent properties of these AIEgens (e.g., quantum yield and emission color) can be easily tuned by adjusting the substituents of the electrophile and nucleophile substrates, exhibiting excellent performance in bio‐imaging. Notably, the mechanistic studies reveal the critical role of β‐H elimination in the formation of the double bond. This contribution provides an efficient method to synthesize poly‐substituted olefins, pushing forward the development of AIEgens.https://doi.org/10.1002/agt2.650aggregation‐induced emissionbio‐imagingcross‐coupling reactionsC−S bond activationpoly‐substituted olefins |
| spellingShingle | Bowei Ma Xinyu Liang Gu Xu Guanghao Zhang Lutang Zhao Liangzhuo Ma Wenbin Xie Xiang Li Qinqin Shi Kaikai Wen Hui Huang General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activation Aggregate aggregation‐induced emission bio‐imaging cross‐coupling reactions C−S bond activation poly‐substituted olefins |
| title | General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activation |
| title_full | General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activation |
| title_fullStr | General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activation |
| title_full_unstemmed | General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activation |
| title_short | General method to synthesize aggregation‐induced emission molecules via carbon‐sulfur bond activation |
| title_sort | general method to synthesize aggregation induced emission molecules via carbon sulfur bond activation |
| topic | aggregation‐induced emission bio‐imaging cross‐coupling reactions C−S bond activation poly‐substituted olefins |
| url | https://doi.org/10.1002/agt2.650 |
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