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Here, we show that heteroatom-controlled resonance-structure selection provides a chemically transparent strategy for tuning excited-state energetics. Comparison of normal-type and iso-type benzannulated five-membered heteroarenes across the NH, O, S, Se, and Te series reveals that heteroatom connectivity governs the redistribution of \u03c0-electron delocalization upon excitation. Iso-type connectivity consistently stabilizes T1 and increases E(S1)\/E(T1), a trend reproduced by vertical TD-DFT, the Zeng\u2013Hoffmann\u2013Ananth scheme, fully adiabatic calculations, and DLPNO-STEOM-CCSD. Calculations on the experimentally established singlet-fission chromophore 1,3-diphenylisobenzofuran further support these protocols as comparative screening tools. Aromaticity and spin-density analyses show that T1 stabilization arises from topology-controlled aromaticity partitioning, whereby the six-membered ring retains local Hu\u0308ckel-like aromatic character while the unpaired electrons are preferentially localized on the adjacent five-membered ring. Chalcogen substitution and functionalization preserve this mechanism, with selected substituted iso-type derivatives satisfying the fully adiabatic 2E(T1) &amp;lt; E(S1) criterion. These results establish resonance-structure control as an electronic-structure principle for identifying compact, tunable singlet-fission chromophore candidates.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01083","type":"journal-article","created":{"date-parts":[[2026,10,2]],"date-time":"2026-10-02T17:01:33Z","timestamp":1790960493000},"page":"13584-13594","source":"Crossref","is-referenced-by-count":0,"title":["Resonance-Structure\nCollapse Enables Aromaticity-Controlled\nDesign of Small Singlet-Fission Chromophore Candidates"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4210-1868","authenticated-orcid":true,"given":"Luis","family":"Leyva-Parra","sequence":"first","affiliation":[{"name":"Universidad Andres Bello , , Avenida Repu\u0301blica 275 , ,","place":["Santiago, Chile, 8370146"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4756-1115","authenticated-orcid":true,"given":"Ricardo","family":"Pino-Rios","sequence":"additional","affiliation":[{"name":"Universidad Andres Bello , , Avenida Repu\u0301blica 275 , ,","place":["Santiago, Chile, 8370146"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,10,2]]},"reference":[{"key":"2026101608081671800_cit1a","doi-asserted-by":"publisher","first-page":"99","DOI":"10.1016\/j.enbuild.2016.06.077","article-title":"A comprehensive review\non design of building integrated photovoltaic system","volume":"128","author":"Shukla","year":"2016","journal-title":"Energy And Build"},{"issue":"4","key":"2026101608081671800_cit1b","doi-asserted-by":"publisher","first-page":"481","DOI":"10.5937\/jaes14-10879","article-title":"An introduction to solar cell technology","volume":"14","author":"Ranabhat","year":"2016","journal-title":"J. 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