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Here, we introduce a hydrogen\u2010bond encoded supramolecular strategy that enables structurally minimal, flexible monomers to assemble into discrete fullerene\u2010binding capsules. The monomer combines intra\u2010 and intermolecular hydrogen\u2010bonding motifs that restrict conformational freedom, induce cyclochirality, and guide controlled self\u2010assembly into oligomeric or cyclic aggregates. Spectroscopic and crystallographic analyses show that guest\u2010induced self\u2010sorting with fullerenes drives the formation of homochiral tetrameric capsules with high binding affinity and distinct structural isomerism. X\u2010ray structures confirm compact host\u2013guest complexes stabilized by cooperative hydrogen bonding and C\u2500H\u00b7\u00b7\u00b7\u03c0 interactions. This work demonstrates that minimal monomer design can encode complex supramolecular behaviour, providing an adaptive platform for molecular recognition, catalysis, and materials science.<\/jats:p>","DOI":"10.1002\/anie.1587126","type":"journal-article","created":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T04:44:06Z","timestamp":1790052246000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Hydrogen\u2010Bond Encoding in a Structurally Minimal Cyclochiral Monomer Enables Assembly of Large Cavities Displaying Supramolecular Isomerism"],"prefix":"10.1002","author":[{"given":"Qixun","family":"Shi","sequence":"first","affiliation":[{"name":"Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Jiangsu National Synergetic Innovation Center For Advanced Materials Nanjing Tech University  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-9268-038X","authenticated-orcid":false,"given":"Liangshun","family":"Guo","sequence":"additional","affiliation":[{"name":"Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Jiangsu National Synergetic Innovation Center For Advanced Materials Nanjing Tech University  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0003-4260-0194","authenticated-orcid":false,"given":"Nojus","family":"Radzevi\u010dius","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Geosciences Vilnius University  Vilnius Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yi","family":"Long","sequence":"additional","affiliation":[{"name":"Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Jiangsu National Synergetic Innovation Center For Advanced Materials Nanjing Tech University  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nana","family":"Zhao","sequence":"additional","affiliation":[{"name":"Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Jiangsu National Synergetic Innovation Center For Advanced Materials Nanjing Tech University  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yue","family":"Cao","sequence":"additional","affiliation":[{"name":"Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Jiangsu National Synergetic Innovation Center For Advanced Materials Nanjing Tech University  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fengxia","family":"Zhu","sequence":"additional","affiliation":[{"name":"Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Jiangsu National Synergetic Innovation Center For Advanced Materials Nanjing Tech University  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vytautas","family":"Klimavicius","sequence":"additional","affiliation":[{"name":"Faculty of Physics Vilnius University  Vilnius Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6992-1620","authenticated-orcid":false,"given":"Gediminas","family":"Kreiza","sequence":"additional","affiliation":[{"name":"Faculty of Physics Vilnius University  Vilnius Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7382-7290","authenticated-orcid":false,"given":"Audrius","family":"Padarauskas","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Geosciences Vilnius University  Vilnius Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chuan","family":"Wang","sequence":"additional","affiliation":[{"name":"Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Jiangsu National Synergetic Innovation Center For Advanced Materials Nanjing Tech University  Nanjing China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7257-5634","authenticated-orcid":false,"given":"Edvinas","family":"Orentas","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry and Geosciences Vilnius University  Vilnius Lithuania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,21]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1007\/978-1-4419-0919-0_1","volume-title":"Recognition Receptors in Biosensors","author":"Kahn K.","year":"2010"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408487"},{"key":"e_1_2_8_4_1","volume-title":"Structure and Mechanism in Protein Science: A Guide to Enzyme Catalysis and Protein Folding","author":"Fersht A.","year":"1999"},{"key":"e_1_2_8_5_1","doi-asserted-by":"crossref","unstructured":"J. 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