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Herein, we focus on a [60]fullerene \u03c0\u2010surface as an electron\u2010deficient aromatics. Using a <jats:sup>1<\/jats:sup>H signal of H<jats:sub>2<\/jats:sub>O@C<jats:sub>60<\/jats:sub> as a magnetic probe, the presence of benzene\u2013fullerene interactions was confirmed. To investigate substituent effects on the noncovalent arene\u2010fullerene interactions, NMR titration experiments were carried out using an open\u2010[60]fullerene and a series of substituted benzenes, i.\u2009e., PhX (X=NO<jats:sub>2<\/jats:sub>, CN, Cl, OMe, H, CH<jats:sub>3<\/jats:sub>, and NH<jats:sub>2<\/jats:sub>), demonstrating a 1\u2009:\u20092 stoichiometry with a positive correlation between stabilization energies upon the first association (\u0394<jats:italic>G<\/jats:italic><jats:sub>1<\/jats:sub>) and Hammet constants (<jats:italic>\u03c3<\/jats:italic><jats:sub>m<\/jats:sub>). The destabilization of the self\u2010assembled structure for X=OMe with a \u03c3\u2010withdrawing nature clearly showed direct through\u2010space substituent\u2010\u03c0 interactions describable by the Wheeler\u2010Houk model while the second association was suggested to be considerably perturbed by the secondary effects.<\/jats:p>","DOI":"10.1002\/asia.202400075","type":"journal-article","created":{"date-parts":[[2024,2,22]],"date-time":"2024-02-22T08:27:22Z","timestamp":1708590442000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Direct Through\u2010Space Substituent\u2010\u03c0 Interactions in Noncovalent Arene\u2013Fullerene Assemblies"],"prefix":"10.1002","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7834-9593","authenticated-orcid":false,"given":"Yoshifumi","family":"Hashikawa","sequence":"first","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0287-0299","authenticated-orcid":false,"given":"Yasujiro","family":"Murata","sequence":"additional","affiliation":[{"name":"Institute for Chemical Research Kyoto University  Uji Kyoto 611-0011 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,3,7]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0022-2836(91)90271-7"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/cs9942300101"},{"key":"e_1_2_8_4_1","unstructured":"\u00a0"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200390319"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00578G"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201906069"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.202300062"},{"key":"e_1_2_8_9_1","unstructured":"\u00a0"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c03024"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c02193"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1039\/B809359H"},{"key":"e_1_2_8_13_1","unstructured":"\u00a0"},{"key":"e_1_2_8_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja049434a"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar3001124"},{"key":"e_1_2_8_16_1","unstructured":"\u00a0"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja016508z"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809720r"},{"key":"e_1_2_8_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja504378p"},{"key":"e_1_2_8_20_1","unstructured":"\u00a0"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199315841"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1039\/b008495f"},{"key":"e_1_2_8_23_1","unstructured":"\u00a0"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00170a016"},{"key":"e_1_2_8_25_2","first-page":"4863","volume":"7","author":"Adams H.","year":"2001","journal-title":"Angew. 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