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A complete study of a series of six naphthothiophene\u2010fused <jats:italic>s<\/jats:italic>\u2010indacene isomers is herein described. Additionally, the structural modifications resulted in increased \u03c0\u2013\u03c0 overlap in the solid state, which was further explored through changing the sterically blocking mesityl group to (triisopropylsilyl)ethynyl in three derivatives. The computed antiaromaticity of the six isomers is compared to the observed physical properties, such as NMR chemical shift, UV\u2010vis, and CV data. We find that the calculations predict the most antiaromatic isomer and give a general estimation of the relative degree of paratropicity for the remaining isomers, when compared to the experimental results.<\/jats:p>","DOI":"10.1002\/chem.202301153","type":"journal-article","created":{"date-parts":[[2023,5,5]],"date-time":"2023-05-05T14:49:34Z","timestamp":1683298174000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Comparison of Antiaromatic Properties in a Series of Structurally Isomeric Naphthothiophene\u2010Fused <i>s<\/i>\u2010Indacenes"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5971-9026","authenticated-orcid":false,"given":"Gabrielle I.","family":"Warren","sequence":"first","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9649-2764","authenticated-orcid":false,"given":"Luca J.","family":"Zocchi","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3340-4645","authenticated-orcid":false,"given":"Lev N.","family":"Zakharov","sequence":"additional","affiliation":[{"name":"Center for Advanced Materials Characterization at Oregon (CAMCOR) University of Oregon  Eugene Oregon 97403-1433 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7027-4141","authenticated-orcid":false,"given":"Michael M.","family":"Haley","sequence":"additional","affiliation":[{"name":"Department of Chemistry &amp; Biochemistry and Materials Science Institute University of Oregon  Eugene Oregon 97403-1253 USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,6,5]]},"reference":[{"key":"e_1_2_8_1_1","volume-title":"Aromaticity: Modern Computational Methods and Applications","author":"Fern\u00e1ndez I.","year":"2021"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00244C"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00392"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300471v"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0103221"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc90288e"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF01339530"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/cen-v043n026.p090"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00993a023"},{"key":"e_1_2_8_10_1","first-page":"64","volume-title":"in Advances in Chemical Physics","author":"Dewar M. 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