High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assembly
Abstract Collecting both enantiomorphs with high optical purity and yield in a single crystallization process can be achieved by adding aggregated polymeric “tailor‐made” additives, known as nano‐splitters. Inefficient preparation and large addition amount have hindered the practical application of...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Wiley
2021-12-01
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| Series: | Aggregate |
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| Online Access: | https://doi.org/10.1002/agt2.129 |
| _version_ | 1819102840299192320 |
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| author | Bowen Li Na Li Zhaoxu Wang Xichong Ye Jie Zhang Xinhua Wan |
| author_facet | Bowen Li Na Li Zhaoxu Wang Xichong Ye Jie Zhang Xinhua Wan |
| author_sort | Bowen Li |
| collection | DOAJ |
| description | Abstract Collecting both enantiomorphs with high optical purity and yield in a single crystallization process can be achieved by adding aggregated polymeric “tailor‐made” additives, known as nano‐splitters. Inefficient preparation and large addition amount have hindered the practical application of such amazing nanoparticles. Herein, we report the first nano‐splitters containing aggregation‐induced emission luminogens prepared via polymerization‐induced self‐assembly of block copolymer, poly[(S)‐2‐(tert‐butoxycarbonylamino)‐6‐(methacrylamido)hexanoic acid]‐b‐polystyrene, followed by the removal of tert‐butoxycarbonyl groups. When added into the supersaturated solution of racemic amino acids (a.a.) with seeds, the fluorescent labeled nano‐assemblies enantioselectivity dyed the crystals of S‐a.a. and enabled the separation from colorless R‐a.a. crystals in terms of fluorescent difference. Both enantiomers were obtained with high optical purity and yield (e.g., R‐ asparagine monohydrate, >99 ee%; S‐ asparagine monohydrate, ∼94 ee%; 88% total yield). Owing to a low detection limit of fluorescence, the addition amount was reduced to 0.03 wt% without remarkably compromising the ee values of both enantiomorphs. Due to the low addition amount and efficient synthesis, the output–input ratio was increased greatly. |
| first_indexed | 2024-12-22T01:40:57Z |
| format | Article |
| id | doaj.art-09a7e6beba634758859f409de994d91d |
| institution | Directory Open Access Journal |
| issn | 2692-4560 |
| language | English |
| last_indexed | 2024-12-22T01:40:57Z |
| publishDate | 2021-12-01 |
| publisher | Wiley |
| record_format | Article |
| series | Aggregate |
| spelling | doaj.art-09a7e6beba634758859f409de994d91d2022-12-21T18:43:13ZengWileyAggregate2692-45602021-12-0126n/an/a10.1002/agt2.129High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assemblyBowen Li0Na Li1Zhaoxu Wang2Xichong Ye3Jie Zhang4Xinhua Wan5Beijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of Education College of Chemistry and Molecular Engineering, Peking University Beijing ChinaBeijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of Education College of Chemistry and Molecular Engineering, Peking University Beijing ChinaBeijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of Education College of Chemistry and Molecular Engineering, Peking University Beijing ChinaBeijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of Education College of Chemistry and Molecular Engineering, Peking University Beijing ChinaBeijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of Education College of Chemistry and Molecular Engineering, Peking University Beijing ChinaBeijing National Laboratory for Molecular Sciences Key Laboratory of Polymer Chemistry and Physics of Ministry of Education College of Chemistry and Molecular Engineering, Peking University Beijing ChinaAbstract Collecting both enantiomorphs with high optical purity and yield in a single crystallization process can be achieved by adding aggregated polymeric “tailor‐made” additives, known as nano‐splitters. Inefficient preparation and large addition amount have hindered the practical application of such amazing nanoparticles. Herein, we report the first nano‐splitters containing aggregation‐induced emission luminogens prepared via polymerization‐induced self‐assembly of block copolymer, poly[(S)‐2‐(tert‐butoxycarbonylamino)‐6‐(methacrylamido)hexanoic acid]‐b‐polystyrene, followed by the removal of tert‐butoxycarbonyl groups. When added into the supersaturated solution of racemic amino acids (a.a.) with seeds, the fluorescent labeled nano‐assemblies enantioselectivity dyed the crystals of S‐a.a. and enabled the separation from colorless R‐a.a. crystals in terms of fluorescent difference. Both enantiomers were obtained with high optical purity and yield (e.g., R‐ asparagine monohydrate, >99 ee%; S‐ asparagine monohydrate, ∼94 ee%; 88% total yield). Owing to a low detection limit of fluorescence, the addition amount was reduced to 0.03 wt% without remarkably compromising the ee values of both enantiomorphs. Due to the low addition amount and efficient synthesis, the output–input ratio was increased greatly.https://doi.org/10.1002/agt2.129aggregation‐induced emission (AIE)chiralconglomeratepolymerization‐induced self‐assemblyRAFTstereoseparation |
| spellingShingle | Bowen Li Na Li Zhaoxu Wang Xichong Ye Jie Zhang Xinhua Wan High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assembly Aggregate aggregation‐induced emission (AIE) chiral conglomerate polymerization‐induced self‐assembly RAFT stereoseparation |
| title | High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assembly |
| title_full | High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assembly |
| title_fullStr | High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assembly |
| title_full_unstemmed | High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assembly |
| title_short | High‐performance nano‐splitters containing aggregation‐induced emission luminogens for stereoselective crystallization obtained via polymerization‐induced self‐assembly |
| title_sort | high performance nano splitters containing aggregation induced emission luminogens for stereoselective crystallization obtained via polymerization induced self assembly |
| topic | aggregation‐induced emission (AIE) chiral conglomerate polymerization‐induced self‐assembly RAFT stereoseparation |
| url | https://doi.org/10.1002/agt2.129 |
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