{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T11:11:15Z","timestamp":1789125075623,"version":"build-2803163510"},"reference-count":20,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T00:00:00Z","timestamp":1789084800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"},{"start":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T00:00:00Z","timestamp":1789084800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["26H02266"],"award-info":[{"award-number":["26H02266"]}],"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":["21H05024"],"award-info":[{"award-number":["21H05024"]}],"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":["21H04690 to T.F"],"award-info":[{"award-number":["21H04690 to T.F"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Controlling the interaction landscape of threefold \u03c0\u2010surfaces offers a promising strategy for directing multidirectional molecular packing. Triptycene\u2010tribenzoquinone, with its rigid three\u2010bladed framework, provides a suitable platform for exploring this concept. Here we report the synthesis of new fluoro\u2010, bromo\u2010, and iodo\u2010substituted triptycene\u2010tribenzoquinones, which, together with the previously reported chloro\u2010substituted derivative, constitute the complete series of hexahalogenated triptycene\u2010tribenzoquinones (\n                    <jats:bold>\n                      TT\n                      <jats:sub>X<\/jats:sub>\n                    <\/jats:bold>\n                    ; X = F, Cl, Br, and I). Using this series, we systematically investigate the effects of peripheral halogenation on their electronic properties and solid\u2010state molecular packing. All derivatives exhibit reversible three\u2010step reduction with first reduction potentials comparable to those of the corresponding tetrahalogenated benzoquinones. Increasing halogen size enhances the anisotropy of the electrostatic surface potential, leading to progressively stronger \u03c3\u2010hole character. Upon crystallization, different packing modes emerge depending on the interplay between the intrinsic threefold \u03c0\u2010surface geometry, halogen size, and \u03c3\u2010hole character, with\n                    <jats:bold>\n                      TT\n                      <jats:sub>F<\/jats:sub>\n                    <\/jats:bold>\n                    ,\n                    <jats:bold>\n                      TT\n                      <jats:sub>Cl<\/jats:sub>\n                    <\/jats:bold>\n                    , and\n                    <jats:bold>\n                      TT\n                      <jats:sub>Br<\/jats:sub>\n                    <\/jats:bold>\n                    , and\n                    <jats:bold>\n                      TT\n                      <jats:sub>I<\/jats:sub>\n                    <\/jats:bold>\n                    forming non\u2010layered packing, layered rectangular 2D sheets, and a porous 3D network, respectively. These results demonstrate that peripheral halogenation reshapes the interaction landscape of threefold \u03c0\u2010surfaces while preserving their intrinsic redox properties, providing a design strategy for organizing molecular building blocks with multidirectional \u03c0\u2010surfaces into desired supramolecular architectures.\n                  <\/jats:p>","DOI":"10.1002\/chem.71692","type":"journal-article","created":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T10:56:53Z","timestamp":1789124213000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Designing Threefold \u03c0\u2010Surfaces Through Peripheral Halogenation to Shape Multidirectional Molecular Packing"],"prefix":"10.1002","author":[{"given":"Shuta","family":"Tsuruga","sequence":"first","affiliation":[{"name":"Laboratory for Chemistry and Life Science Institute of Integrated Research Institute of Science Tokyo  Yokohama Japan"},{"name":"Department of Chemical Science and Engineering School of Materials and Chemical Technology Institute of Science Tokyo  Yokohama Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenzo","family":"Suzuki","sequence":"additional","affiliation":[{"name":"Laboratory for Chemistry and Life Science Institute of Integrated Research Institute of Science Tokyo  Yokohama Japan"},{"name":"Department of Chemical Science and Engineering School of Materials and Chemical Technology Institute of Science Tokyo  Yokohama Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2798-1203","authenticated-orcid":false,"given":"Hiromichi","family":"Yokoyama","sequence":"additional","affiliation":[{"name":"Laboratory for Chemistry and Life Science Institute of Integrated Research Institute of Science Tokyo  Yokohama Japan"},{"name":"Department of Chemical Science and Engineering School of Materials and Chemical Technology Institute of Science Tokyo  Yokohama Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8437-1965","authenticated-orcid":false,"given":"Yoshiaki","family":"Shoji","sequence":"additional","affiliation":[{"name":"Laboratory for Chemistry and Life Science Institute of Integrated Research Institute of Science Tokyo  Yokohama Japan"},{"name":"Department of Chemical Science and Engineering School of Materials and Chemical Technology Institute of Science Tokyo  Yokohama Japan"},{"name":"Research Center for Autonomous Systems Materialogy (ASMat) Institute of Integrated Research Institute of Science Tokyo  Yokohama Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5586-9238","authenticated-orcid":false,"given":"Takanori","family":"Fukushima","sequence":"additional","affiliation":[{"name":"Laboratory for Chemistry and Life Science Institute of Integrated Research Institute of Science Tokyo  Yokohama Japan"},{"name":"Department of Chemical Science and Engineering School of Materials and Chemical Technology Institute of Science Tokyo  Yokohama Japan"},{"name":"Research Center for Autonomous Systems Materialogy (ASMat) Institute of Integrated Research Institute of Science Tokyo  Yokohama Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,11]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/b900754g"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41428\u2010024\u201000920\u2010x"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.4c00743"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.202000161"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02706"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040\u20104039(99)01196\u2010X"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/c8cc00753e"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/c7ta09968a"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1246\/cl.210219"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/c8ce00697k"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00484"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1351\/PAC\u2010REC\u201012\u201005\u201010"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397911.2022.2077115"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja02206a016"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202211688"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00002a004"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/b818330a"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576721002910"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3dt50599e"},{"key":"e_1_2_7_21_1","unstructured":"Deposition numbers 2577714 (forTTF) 2577715 (forTTBr) and 2577716 (forTTI) 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. The crystallographic data forTTClwere reported previously [9]and are available under deposition number 2072779."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71692","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.71692","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.71692","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,11]],"date-time":"2026-09-11T10:56:55Z","timestamp":1789124215000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.71692"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,11]]},"references-count":20,"alternative-id":["10.1002\/chem.71692"],"URL":"https:\/\/doi.org\/10.1002\/chem.71692","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,11]]},"assertion":[{"value":"2026-08-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-07","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-11","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71692"}}