{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:34:45Z","timestamp":1760315685434,"version":"build-2065373602"},"reference-count":108,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2024,11,21]],"date-time":"2024-11-21T00:00:00Z","timestamp":1732147200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["DFG project INST 271\/444-1; BI1337\/17-1, BI1337\/18-1,BI1337\/16-1; BI 1337\/14-1; the GRK 2670, W69000789, ProjectNr 436494874"],"award-info":[{"award-number":["DFG project INST 271\/444-1; BI1337\/17-1, BI1337\/18-1,BI1337\/16-1; BI 1337\/14-1; the GRK 2670, W69000789, ProjectNr 436494874"]}],"id":[{"id":"10.13039\/501100001659","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":[[2025,2,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The molecular environment around supramolecular bonding systems significantly affects their stability and the assembly of host\u2013guest complexes, most prominent for hydrogen bonds (H\u2010bonds). Hamilton receptor\u2010barbiturate host\u2013guest complexes are well\u2010known in solution, typically forming a 1\u2009:\u20091 molar ratio complex. However, within a polymer matrix, these complexes can form higher\u2010order assemblies, deviating from the standard 1\u2009:\u20091 complex, which are challenging to characterize and often require lab\u2010intensive methods. In this study, a novel Hamilton receptor (<jats:bold>H<\/jats:bold>) was equipped with cyclopentene moieties and used as a host to form host\u2013guest complexes (<jats:bold>H\u2212B<\/jats:bold>) with allobarbital (<jats:bold>B<\/jats:bold>), followed by covalent crosslinking. UV\u2010Vis spectroscopy titration experiments in different solvents and at various temperatures revealed that polar solvents containing additional H\u2010bonding sites significantly reduce the formation of the 1\u2009:\u20091 <jats:bold>H\u2212B<\/jats:bold> complex, as indicated by a reduced association constant. Higher\u2010order aggregates (<jats:bold>HH<\/jats:bold>\u2010dimer, <jats:bold>HHH<\/jats:bold>\u2010trimer) were subsequently detected via an alkene cross\u2010metathesis (<jats:bold>CM<\/jats:bold>) reaction to fix the assemblies covalently, followed by analysis via electrospray ionization mass spectrometry (ESI MS). This two\u2010step method, firstly via <jats:bold>CM<\/jats:bold> fixation followed by ESI MS, was extended to study the <jats:bold>H\u2212B<\/jats:bold> model complex within a polyisobutylene (<jats:bold>PIB<\/jats:bold>) matrix, presenting a direct method to analyze the complex host\u2013guest assembly in solvent\u2010free (polymer) environments.<\/jats:p>","DOI":"10.1002\/chem.202403939","type":"journal-article","created":{"date-parts":[[2024,11,12]],"date-time":"2024-11-12T05:04:56Z","timestamp":1731387896000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Proximity Effects and Aggregation of Hamilton\u2010Receptor Barbiturate Host\u2013Guest Complexes Probed by Cross\u2010Metathesis and ESI MS Analysis"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2602-2350","authenticated-orcid":false,"given":"Chenming","family":"Li","sequence":"first","affiliation":[{"name":"Faculty of Natural Science II Institute of Chemistry, Macromolecular Chemistry Martin Luther University Halle-Wittenberg  von-Danckelmann-Platz\u20054 Halle\/Saale D-06120 Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pascal","family":"Mai","sequence":"additional","affiliation":[{"name":"Faculty of Natural Science II Institute of Chemistry, Macromolecular Chemistry Martin Luther University Halle-Wittenberg  von-Danckelmann-Platz\u20054 Halle\/Saale D-06120 Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Niclas","family":"Festag","sequence":"additional","affiliation":[{"name":"Faculty of Natural Science II Institute of Chemistry, Macromolecular Chemistry Martin Luther University Halle-Wittenberg  von-Danckelmann-Platz\u20054 Halle\/Saale D-06120 Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2625-4653","authenticated-orcid":false,"given":"Anja","family":"Marinow","sequence":"additional","affiliation":[{"name":"Faculty of Natural Science II Institute of Chemistry, Macromolecular Chemistry Martin Luther University Halle-Wittenberg  von-Danckelmann-Platz\u20054 Halle\/Saale D-06120 Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3834-5445","authenticated-orcid":false,"given":"Wolfgang H.","family":"Binder","sequence":"additional","affiliation":[{"name":"Faculty of Natural Science II Institute of Chemistry, Macromolecular Chemistry Martin Luther University Halle-Wittenberg  von-Danckelmann-Platz\u20054 Halle\/Saale D-06120 Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,11,21]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1205962"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201707363"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00174"},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1PY00198A"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.trechm.2020.09.005"},{"key":"e_1_2_7_7_1","unstructured":"\u00a0"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.3390\/polym14194090"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202203876"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.3390\/ijms222312679"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.19960021118"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201504136"},{"key":"e_1_2_7_13_1","unstructured":"\u00a0"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.6b02507"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SM01304C"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma402007f"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3py00362k"},{"key":"e_1_2_7_18_1","unstructured":"\u00a0"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3py00362k"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja000435m"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.125.127801"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200501505"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ma060838s"},{"key":"e_1_2_7_24_1","unstructured":"\u00a0"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma101962y"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.2c00645"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.1c00120"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.9b02085"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.5b00757"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma402368s"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma901668w"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1038\/srep32356"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.polymer.2016.08.046"},{"key":"e_1_2_7_34_1","unstructured":"\u00a0"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.3c02535"},{"key":"e_1_2_7_36_2","first-page":"840","volume":"52","author":"Wang F.","year":"2021","journal-title":"Acta Polym. Sin."},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.125.127801"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma300534t"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma070485c"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/marc.202300464"},{"key":"e_1_2_7_41_1","unstructured":"\u00a0"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.1c00655"},{"key":"e_1_2_7_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma401714r"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma400622w"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1PY00513H"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jcis.2022.10.029"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.reactfunctpolym.2021.105031"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00174"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00212a065"},{"key":"e_1_2_7_50_1","unstructured":"\u00a0"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b00978"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC09198A"},{"key":"e_1_2_7_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo402500a"},{"key":"e_1_2_7_54_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200461946"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1039\/b009820p"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/om034217o"},{"key":"e_1_2_7_57_1","unstructured":"\u00a0"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jpca.7b11674"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo1006587"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1080\/10610278.2015.1122194"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0700153"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/om020364v"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300389"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0602413103"},{"key":"e_1_2_7_65_1","unstructured":"\u00a0"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1007\/BF01112780"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00020a027"},{"key":"e_1_2_7_68_1","unstructured":"\u00a0"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200601044"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800940j"},{"key":"e_1_2_7_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202102581"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.9b13900"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101937w"},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.08.054"},{"key":"e_1_2_7_75_1","unstructured":"\u00a0"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.6b01410"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma2004184"},{"key":"e_1_2_7_78_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.nanolett.5b05203"},{"volume-title":"Handbook of Organic Solvent Properties","year":"1996","author":"Smallwood I. M.","key":"e_1_2_7_79_1"},{"key":"e_1_2_7_80_1","doi-asserted-by":"publisher","DOI":"10.1039\/C0CS00062K"},{"key":"e_1_2_7_81_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC03888C"},{"key":"e_1_2_7_82_1","unstructured":"\u00a0"},{"key":"e_1_2_7_83_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200301739"},{"key":"e_1_2_7_84_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604966"},{"key":"e_1_2_7_85_1","unstructured":"\u00a0"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3124187"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.vibspec.2016.07.001"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201606012"},{"key":"e_1_2_7_89_1","doi-asserted-by":"publisher","DOI":"10.1039\/b615537e"},{"key":"e_1_2_7_90_1","unstructured":"\u00a0"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/jssc.201100029"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.molpharmaceut.1c00664"},{"key":"e_1_2_7_93_1","unstructured":"\u00a0"},{"key":"e_1_2_7_94_2","first-page":"227","author":"Wang H.","year":"2009","journal-title":"Humana Press"},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.2c00215"},{"key":"e_1_2_7_96_1","unstructured":"\u00a0"},{"key":"e_1_2_7_97_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.3c03428"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-014-5096-9"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2010.10.060"},{"key":"e_1_2_7_100_1","unstructured":"\u00a0"},{"key":"e_1_2_7_101_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7PY01577A"},{"key":"e_1_2_7_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.8b05617"},{"key":"e_1_2_7_103_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.2c05531"},{"key":"e_1_2_7_104_1","unstructured":"\u00a0"},{"key":"e_1_2_7_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00359a020"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200300389"},{"key":"e_1_2_7_107_2","doi-asserted-by":"publisher","DOI":"10.1002\/marc.201900467"},{"key":"e_1_2_7_108_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197508011"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202403939","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T12:31:10Z","timestamp":1760272270000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202403939"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,11,21]]},"references-count":108,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2025,2,6]]}},"alternative-id":["10.1002\/chem.202403939"],"URL":"https:\/\/doi.org\/10.1002\/chem.202403939","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"type":"print","value":"0947-6539"},{"type":"electronic","value":"1521-3765"}],"subject":[],"published":{"date-parts":[[2024,11,21]]},"assertion":[{"value":"2024-10-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-11-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202403939"}}