{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T09:32:41Z","timestamp":1762248761781,"version":"build-2065373602"},"reference-count":40,"publisher":"Wiley","issue":"21","license":[{"start":{"date-parts":[[2025,9,15]],"date-time":"2025-09-15T00:00:00Z","timestamp":1757894400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2025,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Tetrathia[8]circulene is a heteroaromatic framework consisting of an eight\u2010membered ring fused with four thiophene and four benzene units, whose electronic properties are highly tunable by peripheral substituents. Herein, we report the synthesis of a perfluorinated tetrathia[8]circulene bearing hexafluorocyclopentene rings via sequential Suzuki\u2013Miyaura and C\u2500H\/C\u2500Cl coupling reactions. Single\u2010crystal X\u2010ray diffraction analysis revealed a highly planar \u03c0\u2010conjugated core with dense F\u00b7\u00b7\u00b7F contacts, leading to a two\u2010dimensional layered and one\u2010dimensional columnar packing structure. UV\u2013vis absorption spectroscopy and cyclic voltammetry demonstrated that the electron\u2010withdrawing hexafluorocyclopentene units substantially lower the LUMO energy level, resulting in a reduced HOMO\u2013LUMO gap and enhanced electron\u2010accepting character. Density functional theory calculations further supported these findings by correlating the perfluoroalkyl annulation with frontier orbital stabilization and excited\u2010state properties.<\/jats:p>","DOI":"10.1002\/asia.202500806","type":"journal-article","created":{"date-parts":[[2025,9,15]],"date-time":"2025-09-15T14:11:56Z","timestamp":1757945516000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis and Characterization of Electron\u2010Deficient Perfluorinated Tetrathia[8]Circulene via Sequential Coupling Reactions"],"prefix":"10.1002","volume":"20","author":[{"given":"Toma","family":"Tanaka","sequence":"first","affiliation":[{"name":"Department of Material Science Graduate School of Science University of Hyogo  Kouto, Kamigori Hyogo 678\u20131297 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroyasu","family":"Murase","sequence":"additional","affiliation":[{"name":"Department of Molecular and Macromolecular Chemistry Graduate School of Engineering Nagoya University  Furo\u2010cho, Chikusa\u2010ku Nagoya 464\u20138603 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5917-8589","authenticated-orcid":false,"given":"Mio","family":"Shimogaki","sequence":"additional","affiliation":[{"name":"Department of Material Science Graduate School of Science University of Hyogo  Kouto, Kamigori Hyogo 678\u20131297 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9026-7045","authenticated-orcid":false,"given":"Osamu","family":"Iwanaga","sequence":"additional","affiliation":[{"name":"Department of Material Science Graduate School of Science University of Hyogo  Kouto, Kamigori Hyogo 678\u20131297 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5321-2205","authenticated-orcid":false,"given":"Hiroshi","family":"Shinokubo","sequence":"additional","affiliation":[{"name":"Department of Molecular and Macromolecular Chemistry Graduate School of Engineering Nagoya University  Furo\u2010cho, Chikusa\u2010ku Nagoya 464\u20138603 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0247-531X","authenticated-orcid":false,"given":"Yoshihiro","family":"Miyake","sequence":"additional","affiliation":[{"name":"Department of Material Science Graduate School of Science University of Hyogo  Kouto, Kamigori Hyogo 678\u20131297 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,9,15]]},"reference":[{"key":"e_1_2_9_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030081s"},{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC02990C"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CP02936A"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol062238j"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol703016g"},{"volume-title":"Polycyclic Aromatic Hydrocarbons","year":"1997","author":"Harvey R. G.","key":"e_1_2_9_6_1"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00076"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr050966z"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200903628"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4CP01700E"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201402051"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200604203"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/b417320c"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/b816624b"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00190"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr068010r"},{"key":"e_1_2_9_17_1","first-page":"498","volume":"27","author":"Hensel T.","year":"2016","journal-title":"Synlett"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC06495E"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.05.019"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201002261"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100966"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201403028"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC06921A"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.9b01655"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505124"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202001934"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01074"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201700729"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03764"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202100454"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1055\/a-1437-9917"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202200244"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.202001129"},{"key":"e_1_2_9_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202005077"},{"key":"e_1_2_9_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.6b02151"},{"key":"e_1_2_9_36_1","unstructured":"Deposition number 2468242 for 1 contains 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_9_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp8111556"},{"key":"e_1_2_9_38_1","unstructured":"G. W.Frisch Trucks H. B.Schlegel G. E.Scuseria M. A.Robb J. R.Cheeseman G.Scalmani V.Barone G. A.Petersson H.Nakatsuji X.Li M.Caricato A. V.Marenich J.Bloino B. G.Janesko R.Gomperts B.Mennucci H. P.Hratchian J. V.Ortiz A. F.Izmaylov J. L.Sonnenberg Williams\u2010Young F.Ding F.Lipparini F.Egidi J.Goings B.Peng A.Petrone T.Henderson D.Ranasinghe V. G.Zakrzewski J.Gao et\u00a0al. Gaussian Inc. Wallingford CT 2019."},{"key":"e_1_2_9_39_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevA.38.3098"},{"key":"e_1_2_9_40_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.37.785"}],"container-title":["Chemistry \u2013 An Asian Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/asia.202500806","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,11,4]],"date-time":"2025-11-04T09:28:30Z","timestamp":1762248510000},"score":1,"resource":{"primary":{"URL":"https:\/\/aces.onlinelibrary.wiley.com\/doi\/10.1002\/asia.202500806"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,9,15]]},"references-count":40,"journal-issue":{"issue":"21","published-print":{"date-parts":[[2025,11]]}},"alternative-id":["10.1002\/asia.202500806"],"URL":"https:\/\/doi.org\/10.1002\/asia.202500806","archive":["Portico"],"relation":{},"ISSN":["1861-4728","1861-471X"],"issn-type":[{"type":"print","value":"1861-4728"},{"type":"electronic","value":"1861-471X"}],"subject":[],"published":{"date-parts":[[2025,9,15]]},"assertion":[{"value":"2025-06-30","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-09-01","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-09-15","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e00806"}}