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Large starphenes have been prepared using convergent syntheses involving transition metal catalyzed cyclotrimerizations of either preformed acenes or arynes. Here, we report a one\u2010pot divergent synthesis of a 13\u2010ring triquinone that is readily converted to a [4.4.4]tridecastarphene derivative. The one\u2010pot procedure involves the sequential reactions of three 1,4\u2010anthraquinones with <jats:italic>o<\/jats:italic>\u2010quinodimethane derivatives that are generated sequentially from a stable, trisulfone precursor. The resulting [4.4.4]tridecastarphene derivative bearing <jats:italic>p<\/jats:italic>\u2010(<jats:italic>t<\/jats:italic>\u2010butyl)phenyl substituents was characterized by <jats:sup>1<\/jats:sup>H\u2005NMR, <jats:sup>13<\/jats:sup>C\u2005NMR and UV\u2010vis spectroscopies, as well as mass spectrometry, cyclic voltammetry and differential pulse voltammetry. Theoretical and experimental studies reveal a relatively high\u2010lying HOMO orbital (about \u22124.70 to \u22124.86\u2005eV) and a relatively small HOMO\u2010LUMO gap (2.1\u2005eV), suggesting utility as a p\u2010type organic semiconductor. Our [4.4.4]tridecastarphene derivative photooxidizes in a CH<jats:sub>2<\/jats:sub>Cl<jats:sub>2<\/jats:sub> solution exposed to ambient light and air with a half\u2010life of 150\u2005minutes at room temperature, but shows no sign of degradation after 12\u2005months in the solid\u2010state. Our [4.4.4]tridecastarphene derivative also shows excellent solubility in a number of organic solvents including dichloromethane, chloroform and toluene, potentially enabling printed electronic applications.<\/jats:p>","DOI":"10.1002\/chem.202402745","type":"journal-article","created":{"date-parts":[[2024,9,21]],"date-time":"2024-09-21T10:25:51Z","timestamp":1726914351000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["One\u2010Pot Divergent Synthesis of a 13\u2010Ring Triquinone and its Facile Conversion to a [4.4.4]Tridecastarphene"],"prefix":"10.1002","volume":"30","author":[{"given":"Hao","family":"Geng","sequence":"first","affiliation":[{"name":"Department of Chemistry University of New Hampshire  23 Academic Way Durham, New Hampshire 03824 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ryan P.","family":"Kopreski","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of New Hampshire  23 Academic Way Durham, New Hampshire 03824 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-1479-1657","authenticated-orcid":false,"given":"Qian","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of New Hampshire  23 Academic Way Durham, New Hampshire 03824 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonathan B.","family":"Briggs","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of New Hampshire  23 Academic Way Durham, New Hampshire 03824 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-7751-3573","authenticated-orcid":false,"given":"Glen P.","family":"Miller","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of New Hampshire  23 Academic Way Durham, New Hampshire 03824 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,11,5]]},"reference":[{"key":"e_1_2_8_1_1","volume-title":"Polycyclic Hydrocarbons","author":"Clar E.","year":"1964"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr990322p"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr030666m"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)96845-0"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1038\/371141a0"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.52.13274"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0390956"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1039\/b417320c"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201000585"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2jm31684f"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-4095(200101)13:2<130::AID-ADMA130>3.0.CO;2-L"},{"key":"e_1_2_8_12_1","doi-asserted-by":"crossref","unstructured":"K. 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