{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T19:09:54Z","timestamp":1791313794906,"version":"4.3.1"},"reference-count":62,"publisher":"Wiley","issue":"47","license":[{"start":{"date-parts":[[2026,7,27]],"date-time":"2026-07-27T00:00:00Z","timestamp":1785110400000},"content-version":"am","delay-in-days":365,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#am"},{"start":{"date-parts":[[2025,7,27]],"date-time":"2025-07-27T00:00:00Z","timestamp":1753574400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["T2325017"],"award-info":[{"award-number":["T2325017"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP24K21247"],"award-info":[{"award-number":["JP24K21247"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP22H00334"],"award-info":[{"award-number":["JP22H00334"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP22K19063"],"award-info":[{"award-number":["JP22K19063"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP22K14725"],"award-info":[{"award-number":["JP22K14725"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003382","name":"Core Research for Evolutional Science and Technology","doi-asserted-by":"publisher","award":["JPMJCR24S6"],"award-info":[{"award-number":["JPMJCR24S6"]}],"id":[{"id":"10.13039\/501100003382","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,8,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Chiral self\u2010sorting, including both narcissistic and social self\u2010sorting, can generate homochiral and heterochiral supramolecular assemblies, respectively. However, achieving control over both pathways through molecular design remains challenging. Herein, we designed a series of macrocyclic pillar[5]arene derivatives with linear chains that thread into the cavities of adjacent molecules in the crystal, forming 1D superstructures. By varying the rigidity of these linear chains, we discovered that the rigidity dictated chiral preference: rigid chains induced homochiral arrangements, whereas flexible chains favored heterochiral arrangements. Mechanistically, the close packing of adjacent pillar[5]arenes through host\u2013guest supramolecular system played a crucial role in controlling the chiral sequence.<\/jats:p>","DOI":"10.1002\/chem.202502040","type":"journal-article","created":{"date-parts":[[2025,7,28]],"date-time":"2025-07-28T06:33:41Z","timestamp":1753684421000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Chirality\u2010Controllable Self\u2010Sorting in Macrocyclic Supramolecular Assemblies: Homochiral and Heterochiral 1D Architectures"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0009-0005-0444-624X","authenticated-orcid":false,"given":"Chenyi","family":"Ma","sequence":"first","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura, Nishikyo\u2010ku Kyoto 615\u20138510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8669-1089","authenticated-orcid":false,"given":"Shunsuke","family":"Ohtani","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura, Nishikyo\u2010ku Kyoto 615\u20138510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weihao","family":"Wang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5348-5521","authenticated-orcid":false,"given":"Kenichi","family":"Kato","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura, Nishikyo\u2010ku Kyoto 615\u20138510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaodong","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  Shanghai 200240 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomoki","family":"Ogoshi","sequence":"additional","affiliation":[{"name":"Department of Synthetic Chemistry and Biological Chemistry Graduate School of Engineering Kyoto University  Katsura, Nishikyo\u2010ku Kyoto 615\u20138510 Japan"},{"name":"WPI Nano Life Science Institute (WPI\u2010NanoLSI) Kanazawa University  Kakuma\u2010machi Kanazawa 920\u20131192 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,27]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00745"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja028913b"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr100357h"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CS00097B"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC05118K"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3SC03685E"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC02259E"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c12525"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/1099-0682(20011)2001:1<201::AID-EJIC201>3.0.CO;2-9"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201605286"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja202696d"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaa4249"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c11452"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202303035"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202407135"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c07291"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c00823"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3SC52449C"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c00586"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja711260m"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4CC01246A"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.2c11776"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.mtchem.2022.100919"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202010802"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201808998"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.xcrp.2023.101637"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacsau.3c00131"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4RA03769C"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.cgd.4c00977"},{"key":"e_1_2_8_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2024.153508"},{"key":"e_1_2_8_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201805733"},{"key":"e_1_2_8_32_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-41713-9"},{"key":"e_1_2_8_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2020.101443"},{"key":"e_1_2_8_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4CC04620J"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC03579D"},{"key":"e_1_2_8_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b08257"},{"key":"e_1_2_8_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CE01416J"},{"key":"e_1_2_8_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC06951B"},{"key":"e_1_2_8_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2022.133240"},{"key":"e_1_2_8_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b13156"},{"key":"e_1_2_8_41_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b02621"},{"key":"e_1_2_8_42_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2CC02255A"},{"key":"e_1_2_8_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201600688"},{"key":"e_1_2_8_44_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0PY00327A"},{"key":"e_1_2_8_45_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c08751"},{"key":"e_1_2_8_46_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-023-40594-2"},{"key":"e_1_2_8_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA09307F"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09757"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cclet.2021.12.010"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1002\/pi.6111"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1039\/b920146g"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC05929E"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC09466J"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0QO00315H"},{"key":"e_1_2_8_55_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202414611"},{"key":"e_1_2_8_56_1","unstructured":"Deposition numbers 2432961 (for1) 2432976 (for2) 2432966 (for3) 2432999 (for4) and 2432967 (for6) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service."},{"key":"e_1_2_8_57_1","doi-asserted-by":"publisher","DOI":"10.1039\/b810189b"},{"key":"e_1_2_8_58_1","unstructured":"We also performed geometry optimization for the homochiral and heterochiral dimers of2and4. However in the optimized dimer structures the pillar\u2010shaped cavity collapsed. As a result we were unable to appropriately compare the energy differences between the homochiral and heterochiral dimers of2and4."},{"key":"e_1_2_8_59_1","volume-title":"Gaussian 16","author":"Frisch M. J.","year":"2016"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/C3CC47379A"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.7b02399"},{"key":"e_1_2_8_62_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsomega.3c03634"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/am-pdf\/10.1002\/chem.202502040","content-type":"application\/pdf","content-version":"am","intended-application":"syndication"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202502040","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T14:29:29Z","timestamp":1760279369000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202502040"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,27]]},"references-count":62,"journal-issue":{"issue":"47","published-print":{"date-parts":[[2025,8,21]]}},"alternative-id":["10.1002\/chem.202502040"],"URL":"https:\/\/doi.org\/10.1002\/chem.202502040","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,27]]},"assertion":[{"value":"2025-06-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-07","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-27","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e02040"}}