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Among these, extrusion processes enable skeletal reorganization through the elimination of small fragments, granting access to otherwise synthetically challenging frameworks. Photoextrusion that results in the formation of carbon\u2013carbon bonds is particularly intriguing due to the possibility of broad applicability in synthetic chemistry. 9,9\u2032-Dianthrylsulfoxide (9-AnSO) undergoes photoinduced sulfur monoxide (SO) extrusion, resulting in C\u2013C bond formation between the two anthracene groups. This transformation could proceed via a concerted SO elimination or stepwise radical pathway, however the excited-state dynamics remain unclear. SO-trapping and spin-trapping experiments on 9-AnSO, supported by EPR and mass spectrometry, confirm the formation of sulfinyl radicals and rule out pathways involving sulfur extrusion as S or SO2. Triplet sensitization experiments and DFT calculations support a triplet-mediated pathway, consistent with the reduced reactivity observed in the presence of oxygen. In contrast, 1,1\u2032- and 2,2\u2032-bridged isomers show no photochemical reactivity, demonstrating strong positional dependence of the C\u2013S homolysis reaction. These findings provide direct evidence for a stepwise radical mechanism for SO extrusion, establish the structural features controlling photochemical C\u2013S bond cleavage in dianthryl sulfoxides, and offer design principles for new light-responsive molecules.<\/jats:p>","DOI":"10.1021\/jacs.6c09333","type":"journal-article","created":{"date-parts":[[2026,8,10]],"date-time":"2026-08-10T14:01:59Z","timestamp":1786370519000},"page":"34678-34686","source":"Crossref","is-referenced-by-count":1,"title":["Elucidating\nthe Mechanism of Photoinduced Sulfur Monoxide\nExtrusion from Dianthryl Sulfoxide"],"prefix":"10.1021","volume":"148","author":[{"given":"Hikaru","family":"Noguchi","sequence":"first","affiliation":[{"name":"University of British Columbia , , , ,","place":["Vancouver, British Columbia, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5302-1660","authenticated-orcid":true,"given":"Cla\u0300udia","family":"Climent","sequence":"additional","affiliation":[{"name":"Universitat de Barcelona , , ,","place":["Barcelona, Spain, 08028"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6675-652X","authenticated-orcid":true,"given":"Ka-Ming","family":"Tong","sequence":"additional","affiliation":[{"name":"University of British Columbia , , , ,","place":["Vancouver, British Columbia, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jennifer","family":"Yuan","sequence":"additional","affiliation":[{"name":"University of British Columbia , , , ,","place":["Vancouver, British Columbia, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3194-8227","authenticated-orcid":true,"given":"Charles J.","family":"Walsby","sequence":"additional","affiliation":[{"name":"Simon Fraser University , , , ,","place":["Burnaby, British Columbia, Canada, V5A 1S6"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Casanova","sequence":"additional","affiliation":[{"name":"Donostia International Physics Center (DIPC) , , ,","place":["Donostia, Euskadi, Spain, 20018"]},{"name":"Basque Foundation for Science , , , ,","place":["Bilbao, Euskadi, Spain, 48009"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3076-790X","authenticated-orcid":true,"given":"Michael O.","family":"Wolf","sequence":"additional","affiliation":[{"name":"University of British Columbia , , , ,","place":["Vancouver, British Columbia, Canada, V6T 1Z1"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,10]]},"reference":[{"key":"2026081910243056800_cit1","first-page":"25","article-title":"Carbon\u2013Carbon\nBond Formation by the Photoelimination of Small Molecules in Solution\nand in Crystals","volume-title":"Handbook of Synthetic\nPhotochemistry","author":"Shiraki","year":"2010"},{"key":"2026081910243056800_cit2","doi-asserted-by":"publisher","first-page":"287","DOI":"10.3762\/bjoc.20.30","article-title":"Synthesis of \u03c0-Conjugated Polycyclic\nCompounds by Late-Stage Extrusion of Chalcogen Fragments","volume":"20","author":"Okba","year":"2024","journal-title":"Beilstein J. 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