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While PAHs have been studied intensively as single units, here PAHs were constructed in ladder\u2010type arrangements using cross\u2010conjugated fulvalene and dithiafulvalene motifs as connecting units and moving forward a convenient synthetic approach for dimerizing (thio)ketones into olefins by the action of Lawesson's reagent. Some of the PAHs can also be regarded as \u201csuper\u2010extended\u201d tetrathiafulvalenes (TTFs) with some of the largest cores ever explored, being multi\u2010redox systems that exhibit both reversible oxidations and reductions. Concomitant absorption redshifts were observed when expanding the ladder\u2010type structures from one to two to three indenofluorene units, and optical and electrochemical HOMO\u2010LUMO gaps were found to correlate linearly. Various conformations (and solid\u2010state packing arrangements) were studied by X\u2010ray crystallography and computations.<\/jats:p>","DOI":"10.1002\/chem.202100984","type":"journal-article","created":{"date-parts":[[2021,4,16]],"date-time":"2021-04-16T08:03:29Z","timestamp":1618560209000},"page":"8315-8324","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":28,"title":["Fulvalene\u2010Based Polycyclic Aromatic Hydrocarbon Ladder\u2010Type Structures: Synthesis and Properties"],"prefix":"10.1002","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0661-6351","authenticated-orcid":false,"given":"Viktor","family":"Bliksted Roug Pedersen","sequence":"first","affiliation":[{"name":"Department of Chemistry University of Copenhagen  Universitetsparken 5 2100 Copenhagen \u00d8 Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8982-4756","authenticated-orcid":false,"given":"Jeppe","family":"Granh\u00f8j","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Copenhagen  Universitetsparken 5 2100 Copenhagen \u00d8 Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4960-8802","authenticated-orcid":false,"given":"Andreas","family":"Erbs Hillers\u2010Bendtsen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Copenhagen  Universitetsparken 5 2100 Copenhagen \u00d8 Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2698-113X","authenticated-orcid":false,"given":"Anders","family":"Kadziola","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Copenhagen  Universitetsparken 5 2100 Copenhagen \u00d8 Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4090-7697","authenticated-orcid":false,"given":"Kurt V.","family":"Mikkelsen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Copenhagen  Universitetsparken 5 2100 Copenhagen \u00d8 Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8377-0788","authenticated-orcid":false,"given":"Mogens","family":"Br\u00f8ndsted Nielsen","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Copenhagen  Universitetsparken 5 2100 Copenhagen \u00d8 Denmark"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,5,19]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0566477"},{"key":"e_1_2_6_3_2","doi-asserted-by":"crossref","unstructured":"T. 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