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In this study, we present a novel class of tripeptide\u2010appended macrocyclic ion channels that undergo aromatic interaction\u2010driven adaptive transformation from unimolecular chloride channels into higher\u2010order nanopores. At low concentrations, analogues with aromatic tripeptide\u2010functionalized macrocycles (\n                    <jats:bold>MC\u2010F<\/jats:bold>\n                    and\n                    <jats:bold>MC\u2010W<\/jats:bold>\n                    ) function as discrete and efficient chloride channels. Upon increasing the concentration, cooperative aromatic interactions among the tripeptide side chains promote their lateral self\u2010assembly into stable nanopores, enabling efficient transmembrane transport of small molecules, including carboxyfluorescein and glucose. In contrast, the aliphatic analogues (\n                    <jats:bold>MC\u2010A<\/jats:bold>\n                    ,\n                    <jats:bold>MC\u2010L<\/jats:bold>\n                    , and\n                    <jats:bold>MC\u2010I<\/jats:bold>\n                    ) remain restricted to unimolecular chloride channels. Single\u2010channel measurements combined with theoretical calculations further substantiate the structural stability and energetic preference of tetrameric and pentameric assemblies within lipid bilayers. Collectively, this work establishes cooperative aromatic interactions as a versatile and robust design principle for engineering adaptive artificial channels, thereby narrowing the functional gap between synthetic systems and the dynamic regulatory behavior of natural channels.\n                  <\/jats:p>","DOI":"10.1002\/anie.7110390","type":"journal-article","created":{"date-parts":[[2026,7,27]],"date-time":"2026-07-27T12:12:04Z","timestamp":1785154324000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Aromatic Interaction\u2010Driven Adaptive Transformation of Macrocyclic Unimolecular Chloride Channels Into Nanopores"],"prefix":"10.1002","volume":"65","author":[{"given":"Xiaopan","family":"Xie","sequence":"first","affiliation":[{"name":"State Key Laboratory of Vaccines for Infectious Diseases Xiang An Biomedicine Laboratory Fujian Provincial Key Laboratory of Innovative Drug Target Research MOE Key Laboratory of Spectrochemical Analysis and Instrumentation School of Pharmaceutical Sciences Xiamen University  Xiamen Fujian China"},{"name":"Shenzhen Research Institute of Xiamen University  Shenzhen Guangdong China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juncheng","family":"Wan","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Vaccines for Infectious Diseases Xiang An Biomedicine Laboratory Fujian Provincial Key Laboratory of Innovative Drug Target Research MOE Key Laboratory of Spectrochemical Analysis and Instrumentation School of Pharmaceutical Sciences Xiamen University  Xiamen Fujian China"},{"name":"Shenzhen Research Institute of Xiamen University  Shenzhen Guangdong China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jin","family":"Zhou","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Vaccines for Infectious Diseases Xiang An Biomedicine Laboratory Fujian Provincial Key Laboratory of Innovative Drug Target Research MOE Key Laboratory of Spectrochemical Analysis and Instrumentation School of Pharmaceutical Sciences Xiamen University  Xiamen Fujian China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zeli","family":"Yu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Vaccines for Infectious Diseases Xiang An Biomedicine Laboratory Fujian Provincial Key Laboratory of Innovative Drug Target Research MOE Key Laboratory of Spectrochemical Analysis and Instrumentation School of Pharmaceutical Sciences Xiamen University  Xiamen Fujian China"},{"name":"Shenzhen Research Institute of Xiamen University  Shenzhen Guangdong China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guanyi","family":"Chen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Vaccines for Infectious Diseases Xiang An Biomedicine Laboratory Fujian Provincial Key Laboratory of Innovative Drug Target Research MOE Key Laboratory of 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