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In this study, we introduce a facile synthesis of Tr\u00f6ger's base (TB)\u2010containing macrocyclic arenes (<jats:bold>TBn<\/jats:bold>), where TB units are linked via methylene bridges, providing the macrocycles with a rigid framework. Oxidation of enantiopure <jats:bold>TBn<\/jats:bold> yields corresponding chiral nitrogen oxides (<jats:bold>TBnNO<\/jats:bold>) with excellent water solubility, attributed to the high polarity of the N\u2212O bond, surpassing the pH limitations of traditional ion\u2010functionalized approaches. Remarkably, <jats:bold>TBnNO<\/jats:bold> exhibits exceptional enantioselective recognition toward a wide range of chiral guests in aqueous solution, achieving enantioselectivities as high as 41.0. The underlying mechanism involves a combination of hydrophobic interactions and steric effects caused by rigid chiral cavities. These findings highlight the potential of nitrogen\u2010oxidized macrocycles as a transformative tool for supramolecular application in water.<\/jats:p>","DOI":"10.1002\/anie.202416975","type":"journal-article","created":{"date-parts":[[2024,10,11]],"date-time":"2024-10-11T00:19:20Z","timestamp":1728605960000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Nitrogen\u2010Oxidized Tr\u00f6ger's Base Macrocyclic Arenes: Unprecedented Enantioselective Recognition in Water"],"prefix":"10.1002","volume":"64","author":[{"given":"Xiaotong","family":"Liang","sequence":"first","affiliation":[{"name":"Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610064 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ting","family":"Zhao","sequence":"additional","affiliation":[{"name":"Changjiang River Scientifc Research Institute of Changjiang Water Resources Commission  Wuhan 430010 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanling","family":"Shen","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610064 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lizhi","family":"Fang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610064 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Long","family":"Chen","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610064 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dayang","family":"Zhou","sequence":"additional","affiliation":[{"name":"Comprehensive Analysis Center ISIR and Department of Applied Chemistry Osaka University Yamada-oka  Suita 565-0871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8969-1148","authenticated-orcid":false,"given":"Wanhua","family":"Wu","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610064 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2049-1324","authenticated-orcid":false,"given":"Cheng","family":"Yang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Chemistry and Technology of Ministry of Education College of Chemistry and State Key Laboratory of Biotherapy Sichuan University  Chengdu 610064 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,9]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00018-008-8002-9"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms7475"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature07370"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00173H"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100357h"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4939-9438-0"},{"key":"e_1_2_7_8_1","unstructured":"\u00a0"},{"key":"e_1_2_7_9_2","first-page":"1","volume":"108","author":"Guy V. 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