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However, transforming [6]helicene into planar coronene typically requires harsh conditions and poses significant challenges. Herein, we demonstrate that replacing the terminal benzene ring of [6]helicene with a thiophene ring enables its photochemical transformation into coronene. Sulfur oxidation of the thiophene ring enables the corresponding thermal transformation, and the terminal tetrafluorination of the opposite benzene ring further accelerates this process, yielding 1,2\u2010difluorocoronene, as confirmed by X\u2010ray crystallography. The transformation begins with an intramolecular Diels\u2013Alder reaction, whose activation energy is significantly lowered by these structural changes. Our findings underscore the utility of strategic modifications such as sulfur oxidation and fluorination in promoting this \u201chelix\u2010to\u2010disc\u201d conversion and opening new avenues for synthesizing functional polycyclic aromatics.<\/jats:p>","DOI":"10.1002\/chem.202402445","type":"journal-article","created":{"date-parts":[[2024,7,25]],"date-time":"2024-07-25T09:58:23Z","timestamp":1721901503000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Helix\u2010to\u2010Disc Conversion of Thia[6]helicenes into Coronenes Facilitated by Sulfur Oxidation and Fluorination"],"prefix":"10.1002","volume":"30","author":[{"given":"Kaito","family":"Seino","sequence":"first","affiliation":[{"name":"Faculty of Science Yamagata University  1-4-12 Kojirakawa-machi, Yamagata Yamagata 990-8560 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tsubasa","family":"Okano","sequence":"additional","affiliation":[{"name":"Faculty of Science Yamagata University  1-4-12 Kojirakawa-machi, Yamagata Yamagata 990-8560 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Koki","family":"Oya","sequence":"additional","affiliation":[{"name":"Faculty of Science Yamagata University  1-4-12 Kojirakawa-machi, Yamagata Yamagata 990-8560 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4100-9995","authenticated-orcid":false,"given":"Hiroshi","family":"Katagiri","sequence":"additional","affiliation":[{"name":"Graduate School of Organic Materials Science Yamagata University  4-3-16 Jonan, Yonezawa Yamagata 992-8510 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7811-1734","authenticated-orcid":false,"given":"Takashi","family":"Murase","sequence":"additional","affiliation":[{"name":"Faculty of Science Yamagata University  1-4-12 Kojirakawa-machi, Yamagata Yamagata 990-8560 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,9,9]]},"reference":[{"key":"e_1_2_9_1_1","unstructured":"\u00a0"},{"key":"e_1_2_9_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01617a097"},{"key":"e_1_2_9_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01599a060"},{"key":"e_1_2_9_4_1","unstructured":"\u00a0"},{"key":"e_1_2_9_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/cber.19320650546"},{"key":"e_1_2_9_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01864a014"},{"key":"e_1_2_9_7_2","doi-asserted-by":"crossref","unstructured":"E. 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