{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T13:04:07Z","timestamp":1790859847595,"version":"4.1.0"},"reference-count":45,"publisher":"Wiley","issue":"52","license":[{"start":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T00:00:00Z","timestamp":1762041600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T00:00:00Z","timestamp":1762041600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["433682494\u2010SFB 1459"],"award-info":[{"award-number":["433682494\u2010SFB 1459"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005156","name":"Alexander von Humboldt-Stiftung","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100005156","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2025,12,22]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Although solvents are central to self\u2010assembly, their chain length has not been recognized as a factor controlling supramolecular polymerization. Herein, we introduce solvent chain length as a key parameter dictating the outcome of supramolecular polymerization. We investigated this phenomenon using a boron dipyrromethene (BODIPY) derivative bearing a phenyl group at the\n                    <jats:italic>meso<\/jats:italic>\n                    \u2010position, amide groups, and solubilizing dodecyloxy side chains (\n                    <jats:bold>1<\/jats:bold>\n                    ). Remarkably, while the shortest liquid alkanes,\n                    <jats:italic>n<\/jats:italic>\n                    \u2010pentane and\n                    <jats:italic>n<\/jats:italic>\n                    \u2010hexane, promote face\u2010to\u2010face (H\u2010type) stacking interactions leading to one\u2010dimensional fiber\u2010like morphologies (\n                    <jats:bold>AggB<\/jats:bold>\n                    ), the longest liquid linear alkane,\n                    <jats:italic>n<\/jats:italic>\n                    \u2010hexadecane, induces a molecular rearrangement into slipped stacks that cannot efficiently grow into extended one\u2010dimensional assemblies, resulting in discrete morphologies (\n                    <jats:bold>AggA<\/jats:bold>\n                    ). In alkanes of intermediate length (C\n                    <jats:sub>7<\/jats:sub>\n                    \u2013C\n                    <jats:sub>15<\/jats:sub>\n                    ), both assembled states coexist to varying degrees, leading to\n                    <jats:italic>concomitant supramolecular polymorphs<\/jats:italic>\n                    , with the slipped packing becoming progressively favored as the chain length increases. Molecular dynamics (MD) simulations reveal that\n                    <jats:bold>AggA<\/jats:bold>\n                    is favored in longer\u2010chain solvents owing to enhanced solvent interactions and conformational freedom of the side chains, while the proximity of aliphatic groups to the aromatic cores attenuates stack elongation. Our findings broaden the role of solvents as design elements in self\u2010assembly and offer new insights into the development of functional supramolecular polymorphs.\n                  <\/jats:p>","DOI":"10.1002\/anie.202520168","type":"journal-article","created":{"date-parts":[[2025,11,3]],"date-time":"2025-11-03T07:21:52Z","timestamp":1762154512000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Solvent Chain Length Directed Supramolecular Polymorphism"],"prefix":"10.1002","volume":"64","author":[{"given":"Zulema","family":"Fern\u00e1ndez","sequence":"first","affiliation":[{"name":"Universit\u00e4t M\u00fcnster Organisch\u2010Chemisches Institut  Corrensstra\u00dfe 36 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Megha","family":"Parashar","sequence":"additional","affiliation":[{"name":"Chemistry and Physics of Materials Unit Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR)  Jakkur Bangalore 560064 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rasitha Manha","family":"Veedu","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster Organisch\u2010Chemisches Institut  Corrensstra\u00dfe 36 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sebastian","family":"Baumert","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster Organisch\u2010Chemisches Institut  Corrensstra\u00dfe 36 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lloren\u00e7","family":"Rubert","sequence":"additional","affiliation":[{"name":"Department of Chemistry Universitat de les Illes Balears  Cra. Valldemossa km 7.5 Palma de Mallorca 07122 Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bartolom\u00e9","family":"Soberats","sequence":"additional","affiliation":[{"name":"Department of Chemistry Universitat de les Illes Balears  Cra. Valldemossa km 7.5 Palma de Mallorca 07122 Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sundaram","family":"Balasubramanian","sequence":"additional","affiliation":[{"name":"Chemistry and Physics of Materials Unit Jawaharlal Nehru Centre for Advanced Scientific Research (JNCASR)  Jakkur Bangalore 560064 India"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6155-8671","authenticated-orcid":false,"given":"Gustavo","family":"Fern\u00e1ndez","sequence":"additional","affiliation":[{"name":"Universit\u00e4t M\u00fcnster Organisch\u2010Chemisches Institut  Corrensstra\u00dfe 36 48149 M\u00fcnster Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,11,2]]},"reference":[{"key":"e_1_2_6_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/ijch.201900165"},{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.202109041"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr400195e"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/pol.20230115"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS00470H"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemmater.4c01265"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201402975"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS00952A"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC02787A"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.202000210"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9PY01342C"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3QO00148B"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2020.213300"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aac7422"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/cm4021172"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41570\u2010019\u20100153\u20108"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201905724"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8RA03225D"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00660"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-020-17356-5"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202105342"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-020-2445-z"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.2c12894"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467\u2010024\u201047874\u20105"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010025\u201001764\u20105"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41557\u2010023\u201001216\u2010y"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c15766"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b11011"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b07697"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b02046"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202213345"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202415774"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.3c07556"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.202403329"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC01636E"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202102183"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2SC00690A"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202509031"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c09293"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202314211"},{"key":"e_1_2_6_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201701299"},{"key":"e_1_2_6_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b07639"},{"key":"e_1_2_6_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC02832J"},{"key":"e_1_2_6_44_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2020.121632"},{"key":"e_1_2_6_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202218555"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202520168","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202520168","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202520168","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T12:46:29Z","timestamp":1780317989000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202520168"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,11,2]]},"references-count":45,"journal-issue":{"issue":"52","published-print":{"date-parts":[[2025,12,22]]}},"alternative-id":["10.1002\/anie.202520168"],"URL":"https:\/\/doi.org\/10.1002\/anie.202520168","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,11,2]]},"assertion":[{"value":"2025-09-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-10-23","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-11-02","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e20168"}}