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The compounds were synthesized in a modular approach via Yamamoto cyclotrimerization of brominated pyracylene precursors, allowing the introduction of electron\u2010withdrawing, \u2010donating, and solubilizing fluoro, methoxy, and <jats:italic>tert<\/jats:italic>\u2010butyl moieties, respectively. The subsequent \u03c0\u2010expansion of the polycyclic scaffold was achieved by oxidative cyclodehydrogenation. X\u2010ray crystallographic analysis revealed the propeller\u2010shaped geometry of the decacyclene core with a pronounced bond length alternation in the central six\u2010membered ring and the columnar packing motif in the solid state. Depending on the substitution pattern, the compounds are capable of up to six reversible reductions within a particularly narrow potential range between \u22121.45 and \u22122.86\u00a0V under electrochemical conditions. This result is in stark contrast to only two reductions of parent decacyclene and clearly demonstrates the major impact of strategic cyclopentannulation on the redox properties of the sp<jats:sup>2<\/jats:sup>\u2010carbon scaffold, which was further supported by density functional theory studies.<\/jats:p>","DOI":"10.1002\/asia.202500551","type":"journal-article","created":{"date-parts":[[2025,6,10]],"date-time":"2025-06-10T11:19:51Z","timestamp":1749554391000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Cyclopentannulated Decacyclenes as Carbon\u2010Based Multistage Electron Acceptors"],"prefix":"10.1002","volume":"20","author":[{"given":"Silas C.","family":"Eiden","sequence":"first","affiliation":[{"name":"Organisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Erik","family":"Misselwitz","sequence":"additional","affiliation":[{"name":"Organisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Frank","family":"Rominger","sequence":"additional","affiliation":[{"name":"Organisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4960-4636","authenticated-orcid":false,"given":"Milan","family":"Kivala","sequence":"additional","affiliation":[{"name":"Organisch\u2010Chemisches Institut Universit\u00e4t Heidelberg  Im Neuenheimer Feld 270 69120 Heidelberg Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,6,10]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200903628"},{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7TC01680H"},{"key":"e_1_2_7_1_3","doi-asserted-by":"publisher","DOI":"10.1039\/C8TC03185A"},{"key":"e_1_2_7_1_4","doi-asserted-by":"publisher","DOI":"10.1039\/C8TC00146D"},{"key":"e_1_2_7_1_5","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00892A"},{"key":"e_1_2_7_1_6","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC03908C"},{"key":"e_1_2_7_1_7","doi-asserted-by":"publisher","DOI":"10.1002\/aenm.202003570"},{"key":"e_1_2_7_1_8","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00535"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja002309o"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja015712j"},{"key":"e_1_2_7_2_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200351253"},{"key":"e_1_2_7_2_4","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200351253"},{"key":"e_1_2_7_2_5","doi-asserted-by":"publisher","DOI":"10.1021\/ja0476258"},{"key":"e_1_2_7_2_6","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200701478"},{"key":"e_1_2_7_2_7","doi-asserted-by":"publisher","DOI":"10.1021\/ja901077a"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja809555c"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200145r"},{"key":"e_1_2_7_3_3","doi-asserted-by":"publisher","DOI":"10.1039\/C4TC02008A"},{"key":"e_1_2_7_3_4","doi-asserted-by":"publisher","DOI":"10.1039\/C9TC04325J"},{"key":"e_1_2_7_3_5","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202002382"},{"key":"e_1_2_7_3_6","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c11608"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201001402"},{"key":"e_1_2_7_4_2","volume":"52","author":"Li H.","year":"2013","journal-title":"Angew. 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