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Combined structural and computational analyses reveal a nearly planar geometry at the central gallium atom, with only minimal distortion toward a trigonal pyramidal geometry, and the unpaired spin density localized in its 4p orbital. Density functional theory (DFT) calculations elucidate the reaction mechanism for the formation of [Li\n                    <jats:sup>+<\/jats:sup>\n                    ]\u2022[\n                    <jats:bold>1<\/jats:bold>\n                    <jats:sup>\u2022\u2212<\/jats:sup>\n                    ], while\n                    <jats:italic>N<\/jats:italic>\n                    \u2010heterocyclic carbene (NHC)\u2010trapping experiments led to the isolation of NHC\u2010stabilized digallyl digallenes (\n                    <jats:bold>2a<\/jats:bold>\n                    and\n                    <jats:bold>2b<\/jats:bold>\n                    ) as well as a digallyl\u2010substituted gallium radical (\n                    <jats:bold>3c<\/jats:bold>\n                    ). Compound [Li\n                    <jats:sup>+<\/jats:sup>\n                    ]\u2022[\n                    <jats:bold>1<\/jats:bold>\n                    <jats:sup>\u2022\u2212<\/jats:sup>\n                    ] exhibits versatile gallium\u2010centered radical reactivity, including one\u2010electron oxidation with S\n                    <jats:sub>8<\/jats:sub>\n                    and facile E\u2500E bond activation (E = S, Se, and I) toward PhS\u2010SPh, PhSe\u2010SePh, and I\n                    <jats:sub>2<\/jats:sub>\n                    .\n                  <\/jats:p>","DOI":"10.1002\/anie.4495111","type":"journal-article","created":{"date-parts":[[2026,7,24]],"date-time":"2026-07-24T10:45:14Z","timestamp":1784889914000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["A Homoleptic Ga\n                    <sub>4<\/sub>\n                    Radical Anion: Isolation, Characterization, and Reactivity"],"prefix":"10.1002","volume":"65","author":[{"given":"Lijie","family":"Pei","sequence":"first","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yushuang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education Guangdong Basic Research Center of Excellence for Functional Molecular Engineering School of Chemistry IGCME Sun Yat\u2010sen University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cong","family":"Fan","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bing","family":"Wang","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenhao","family":"Chen","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ning","family":"Zhang","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Linfang","family":"Lu","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min","family":"Jiang","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhigang","family":"Ni","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gengwen","family":"Tan","sequence":"additional","affiliation":[{"name":"Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education Guangdong Basic Research Center of Excellence for Functional Molecular Engineering School of Chemistry IGCME Sun Yat\u2010sen University  Guangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Di","family":"Wu","sequence":"additional","affiliation":[{"name":"College of Material Chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material Technology Ministry of Education Hangzhou Normal University  Hangzhou 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Numbers 2291197 (3c) 2526482 ([Li+]\u2022[1\u2022\u2212]) 2526483 (4) 2526484 (5) 2526485 (6) 2526486 (7) 2526487 (2a) 2526488 (2b) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre (CCDC) and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk\/structures.www.ccdc.cam.ac.uk\/structures."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.4495111","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.4495111","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.4495111","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T14:42:53Z","timestamp":1790001773000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.4495111"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,7,24]]},"references-count":56,"journal-issue":{"issue":"39","published-print":{"date-parts":[[2026,9,21]]}},"alternative-id":["10.1002\/anie.4495111"],"URL":"https:\/\/doi.org\/10.1002\/anie.4495111","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,7,24]]},"assertion":[{"value":"2026-03-31","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-09","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-07-24","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e4495111"}}