Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine
Abstract Enantioselective recognition and separation are the most important issues in the fields of chemistry, pharmacy, agrochemical, and food science. Here, we developed two optically active diamines showing aggregation‐induced emission (AIE) that can discriminate 5 kinds of chiral acids with high...
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| Format: | Article |
| Language: | English |
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Wiley
2023-06-01
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| Series: | Aggregate |
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| Online Access: | https://doi.org/10.1002/agt2.299 |
| _version_ | 1797797902236516352 |
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| author | Chunxuan Qi Keyue Wei Qingyang Li Yuemei Li Xiaolong Su Jun‐Cheng Yang Jingjing Tian Pu Chen Hai‐Tao Feng Ben Zhong Tang |
| author_facet | Chunxuan Qi Keyue Wei Qingyang Li Yuemei Li Xiaolong Su Jun‐Cheng Yang Jingjing Tian Pu Chen Hai‐Tao Feng Ben Zhong Tang |
| author_sort | Chunxuan Qi |
| collection | DOAJ |
| description | Abstract Enantioselective recognition and separation are the most important issues in the fields of chemistry, pharmacy, agrochemical, and food science. Here, we developed two optically active diamines showing aggregation‐induced emission (AIE) that can discriminate 5 kinds of chiral acids with high enantioselectivity. Especially, a very high fluorescence intensity ratio (Il/Id) of 281 for (±)‐Dibenzoyl‐d/l‐tartaric acid was obtained through the collection of fluorescence change after interaction with chiral AIE‐active diamine. By virtue of AIE property and intermolecular acid‐base interaction, enantioselective separation was facilely realized by simple filtration of the precipitates formed by chiral AIE luminogen (AIEgen) and one enantiomer in the racemic solution. The chiral HPLC data indicated that the precipitates of AIEgen/chiral acid possessed 82% l‐analyte (the enantiomeric excess value was assessed to be 64% ee). Therefore, this method can serve as a simple, convenient, and low‐cost tool for chiral detection and separation. |
| first_indexed | 2024-03-13T03:55:22Z |
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| id | doaj.art-e46f0383bb8d4447b3d3798684797253 |
| institution | Directory Open Access Journal |
| issn | 2692-4560 |
| language | English |
| last_indexed | 2024-03-13T03:55:22Z |
| publishDate | 2023-06-01 |
| publisher | Wiley |
| record_format | Article |
| series | Aggregate |
| spelling | doaj.art-e46f0383bb8d4447b3d37986847972532023-06-22T06:24:45ZengWileyAggregate2692-45602023-06-0143n/an/a10.1002/agt2.299Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamineChunxuan Qi0Keyue Wei1Qingyang Li2Yuemei Li3Xiaolong Su4Jun‐Cheng Yang5Jingjing Tian6Pu Chen7Hai‐Tao Feng8Ben Zhong Tang9AIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaAIE Research Center Shaanxi Key Laboratory of Phytochemistry College of Chemistry and Chemical Engineering Baoji University of Arts and Sciences Baoji ChinaShenzhen Institute of Molecular Aggregate Science and Engineering School of Science and Engineering The Chinese University of Hong Kong‐Shenzhen Shenzhen ChinaAbstract Enantioselective recognition and separation are the most important issues in the fields of chemistry, pharmacy, agrochemical, and food science. Here, we developed two optically active diamines showing aggregation‐induced emission (AIE) that can discriminate 5 kinds of chiral acids with high enantioselectivity. Especially, a very high fluorescence intensity ratio (Il/Id) of 281 for (±)‐Dibenzoyl‐d/l‐tartaric acid was obtained through the collection of fluorescence change after interaction with chiral AIE‐active diamine. By virtue of AIE property and intermolecular acid‐base interaction, enantioselective separation was facilely realized by simple filtration of the precipitates formed by chiral AIE luminogen (AIEgen) and one enantiomer in the racemic solution. The chiral HPLC data indicated that the precipitates of AIEgen/chiral acid possessed 82% l‐analyte (the enantiomeric excess value was assessed to be 64% ee). Therefore, this method can serve as a simple, convenient, and low‐cost tool for chiral detection and separation.https://doi.org/10.1002/agt2.299acid−base interactionaggregation‐induced emissionchiralityenantioselective recognitionfluorescent probe |
| spellingShingle | Chunxuan Qi Keyue Wei Qingyang Li Yuemei Li Xiaolong Su Jun‐Cheng Yang Jingjing Tian Pu Chen Hai‐Tao Feng Ben Zhong Tang Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine Aggregate acid−base interaction aggregation‐induced emission chirality enantioselective recognition fluorescent probe |
| title | Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine |
| title_full | Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine |
| title_fullStr | Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine |
| title_full_unstemmed | Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine |
| title_short | Visualization of enantioselective recognition and separation of chiral acids by aggregation‐induced emission chiral diamine |
| title_sort | visualization of enantioselective recognition and separation of chiral acids by aggregation induced emission chiral diamine |
| topic | acid−base interaction aggregation‐induced emission chirality enantioselective recognition fluorescent probe |
| url | https://doi.org/10.1002/agt2.299 |
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