{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T18:47:33Z","timestamp":1790102853701,"version":"4.0.1"},"reference-count":71,"publisher":"American Chemical Society (ACS)","issue":"31","license":[{"start":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T00:00:00Z","timestamp":1785283200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T00:00:00Z","timestamp":1785283200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T00:00:00Z","timestamp":1785283200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22422105"],"award-info":[{"award-number":["22422105"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Innovation Program of Shanghai Municipal Education Commission","award":["2025GDZKZD02"],"award-info":[{"award-number":["2025GDZKZD02"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Triangulene, known as Clar\u2019s hydrocarbon, is one of the most iconic non-Kekule\u0301 polycyclic benzenoid hydrocarbons, yet solution-phase triangulene dimers have remained experimentally inaccessible despite extensive surface studies. Here, we report the solution synthesis, isolation, and single-crystal structural characterization of a kinetically stabilized \u03b2\u2013\u03b2-linked triangulene dimer, TRI-d. A \u03b2-position covalent linkage combined with bulky substituents inhibits undesired covalent radical recombination and provides kinetic protection for the open-shell framework, resulting in enhanced stability of TRI-d under ambient conditions. In the solid state, TRI-d adopts a distinctly twisted geometry composed of two well-defined triangulene motifs, in contrast to the largely planar surface-bound dimers. Pulsed EPR and magnetic measurements reveal weak antiferromagnetic coupling between the two S = 1 units (J = \u22123.47 meV), producing a singlet ground state and a quintet excited state separated by a small gap (\u0394ES-Q = \u22120.16 kcal mol\u20131), consistent with theory and significantly weaker than in surface-supported analogues. Because of this weak interaction, the S = 2 state is directly detectable by cw-EPR spectroscopy. TRI-d further exhibits millisecond spin\u2013lattice relaxation (T1 = 5.6 ms at 10 K) and microsecond coherence (Tm = 2.24 \u03bcs), highlighting its promise for constructing higher-order triangulene oligomers and exploring quantum spin functionalities.<\/jats:p>","DOI":"10.1021\/jacs.6c08067","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T13:18:10Z","timestamp":1785849490000},"page":"33377-33386","source":"Crossref","is-referenced-by-count":2,"title":["Solution-Synthesized,\nCrystallographically Characterized\n[3]Triangulene Dimer Tetraradical with an Open-Shell Singlet Ground\nState"],"prefix":"10.1021","volume":"148","author":[{"given":"Yiming","family":"Yang","sequence":"first","affiliation":[{"name":"East China Normal University , , ,","place":["Shanghai, China, 200062"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qi","family":"Xiong","sequence":"additional","affiliation":[{"name":"South China University of Technology , , ,","place":["Guangzhou, China, 510641"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yeda","family":"Ding","sequence":"additional","affiliation":[{"name":"East China Normal University , , ,","place":["Shanghai, China, 200062"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shengning","family":"Zhao","sequence":"additional","affiliation":[{"name":"South China University of Technology , , ,","place":["Guangzhou, China, 510641"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junyao","family":"Jiang","sequence":"additional","affiliation":[{"name":"East China Normal University , , ,","place":["Shanghai, China, 200062"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zongtao","family":"Zhu","sequence":"additional","affiliation":[{"name":"East China Normal University , , ,","place":["Shanghai, China, 200062"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4458-6432","authenticated-orcid":true,"given":"Xiao-Li","family":"Zhao","sequence":"additional","affiliation":[{"name":"East China Normal University , , ,","place":["Shanghai, China, 200062"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shang-Da","family":"Jiang","sequence":"additional","affiliation":[{"name":"South China University of Technology , , ,","place":["Guangzhou, China, 510641"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hai-Bo","family":"Yang","sequence":"additional","affiliation":[{"name":"East China Normal University , , ,","place":["Shanghai, China, 200062"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xueliang","family":"Shi","sequence":"additional","affiliation":[{"name":"East China Normal University , , ,","place":["Shanghai, China, 200062"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,29]]},"reference":[{"key":"2026081210083794400_cit1","doi-asserted-by":"publisher","first-page":"2667","DOI":"10.1021\/ja01107a035","article-title":"Aromatic Hydrocarbons. 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Nanotechnol."},{"key":"2026081210083794400_cit5","first-page":"2413","article-title":"Physics and\nChemistry of Two-Dimensional\nTriangulene Crystals","volume":"57","author":"Yu","year":"2024","journal-title":"Acc. Chem. Res."},{"key":"2026081210083794400_cit6","doi-asserted-by":"publisher","first-page":"61","DOI":"10.1021\/acs.accounts.4c00557","article-title":"Physics and\nChemistry of Two-Dimensional\nTriangulene-Based Lattices","volume":"58","author":"Yu","year":"2025","journal-title":"Acc. Chem. Res."},{"key":"2026081210083794400_cit7","doi-asserted-by":"publisher","first-page":"297","DOI":"10.1007\/BF00549259","article-title":"Multiplicity\nof the Ground State of Large Alternant Organic Molecules with Conjugated\nBonds","volume":"47","author":"Ovchinnikov","year":"1978","journal-title":"Theor. Chim. 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Soc., Perkin Trans."},{"issue":"2","key":"2026081210083794400_cit23","doi-asserted-by":"publisher","first-page":"147","DOI":"10.1039\/a606932k","article-title":"The Synthesis\nof Singlet Ground State Derivatives of Non-Kekule\u0301 Polynuclear\nAromatics","author":"Allinson","year":"1997","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"2026081210083794400_cit24","doi-asserted-by":"publisher","first-page":"7658","DOI":"10.1002\/anie.201913783","article-title":"Triangulenes: From\nPrecursor Design to On-Surface Synthesis and Characterization","volume":"59","author":"Su","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210083794400_cit25","doi-asserted-by":"publisher","first-page":"12041","DOI":"10.1002\/anie.202002687","article-title":"Collective All-Carbon\nMagnetism in Triangulene Dimers","volume":"59","author":"Mishra","year":"2020","journal-title":"Angew. Chem.,\nInt. 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Sci."},{"key":"2026081210083794400_cit29","doi-asserted-by":"publisher","first-page":"489","DOI":"10.1038\/nature17151","article-title":"On-Surface Synthesis of Graphene Nanoribbons with Zigzag Edge Topology","volume":"531","author":"Ruffieux","year":"2016","journal-title":"Nature"},{"key":"2026081210083794400_cit30","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevResearch.5.043226","article-title":"Broken-Symmetry\nMagnetic Phases in Two-Dimensional Triangulene Crystals","volume":"5","author":"Catarina","year":"2023","journal-title":"Phys. Rev. Res."},{"key":"2026081210083794400_cit31","doi-asserted-by":"publisher","first-page":"4522","DOI":"10.1021\/jacs.1c12618","article-title":"Aza-Triangulene:\nOn-Surface Synthesis and Electronic and Magnetic Properties","volume":"144","author":"Wang","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"2026081210083794400_cit32","first-page":"11461","article-title":"Surface-Assisted\nFormation of Graphene Nanoribbons","volume":"136","author":"Treier","year":"2014","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081210083794400_cit33","doi-asserted-by":"publisher","first-page":"2390","DOI":"10.1002\/slct.201703054","article-title":"Tailoring the Electronic\nand Magnetic Properties of Peculiar Triplet Ground State Polybenzoid\n\u201cTriangulene\u201d","volume":"3","author":"Sharma","year":"2018","journal-title":"ChemistrySelect"},{"key":"2026081210083794400_cit34","doi-asserted-by":"publisher","first-page":"25224","DOI":"10.1002\/anie.202108301","article-title":"On-Surface\nSynthesis and Collective Spin Excitations of a Triangulene-Based Nanostar","volume":"60","author":"Hieulle","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210083794400_cit35","article-title":"The Aromatic Sextet","author":"Clar","year":"1972"},{"key":"2026081210083794400_cit36","first-page":"151","article-title":"Polycyclic\nHydrocarbons and Aromaticity","volume":"86","author":"Clar","year":"1953","journal-title":"Chem. Ber."},{"key":"2026081210083794400_cit37","doi-asserted-by":"publisher","first-page":"3019","DOI":"10.1039\/D2CC00352J","article-title":"Tri-mesityltriangulene:\nA Persistent Derivative of Clar\u2019s Hydrocarbon","volume":"58","author":"Valenta","year":"2022","journal-title":"Chem. Commun."},{"key":"2026081210083794400_cit38","doi-asserted-by":"publisher","first-page":"39","DOI":"10.3390\/chemistry7020039","article-title":"2,4,6-Trichlorophenyl-Substituted\n[3]Triangulene with Enhanced Stability","volume":"7","author":"Yang","year":"2025","journal-title":"Chemistry"},{"key":"2026081210083794400_cit39","doi-asserted-by":"publisher","first-page":"301","DOI":"10.1038\/s41557-019-0232-y","article-title":"Molecular Spins for\nQuantum Computation","volume":"11","author":"Gaita-Arin\u0303o","year":"2019","journal-title":"Nat. Chem."},{"key":"2026081210083794400_cit40","doi-asserted-by":"publisher","first-page":"87","DOI":"10.1038\/s41578-019-0146-8","article-title":"Molecular\nMagnetism: From Chemical Design to Spin Control","volume":"5","author":"Coronado","year":"2020","journal-title":"Nat. Rev. Mater."},{"key":"2026081210083794400_cit41","doi-asserted-by":"publisher","first-page":"18529","DOI":"10.1039\/D2CP02915D","article-title":"Spin Engineering of Triangulenes\nand Application for Nano Nonlinear\nOptical Materials Design","volume":"24","author":"Yang","year":"2022","journal-title":"Phys. Chem. Chem.\nPhys."},{"key":"2026081210083794400_cit42","doi-asserted-by":"publisher","first-page":"15879","DOI":"10.1021\/jacs.4c02386","article-title":"Regioselective On-Surface Synthesis\nof [3]Triangulene\nGraphene Nanoribbons","volume":"146","author":"Daugherty","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026081210083794400_cit43","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202501874","article-title":"Reactivity and Magnetic\nCoupling\nof Triangulene Dimers Linked via para-Biphenyl Units","volume":"64","author":"Pe\u0301rez-Elvira","year":"2025","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210083794400_cit44","doi-asserted-by":"publisher","first-page":"19303","DOI":"10.1021\/jacs.3c05178","article-title":"Magnetic Coupling\nControl in Triangulene Dimers","volume":"145","author":"Yu","year":"2023","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081210083794400_cit45","doi-asserted-by":"publisher","first-page":"3486","DOI":"10.1021\/acs.jctc.3c00175","article-title":"Predicting Magnetic Coupling and Spin-Polarization\nEnergy in Triangulene Analogues","volume":"19","author":"Yu","year":"2023","journal-title":"J. Chem. Theory\nComput."},{"key":"2026081210083794400_cit46","doi-asserted-by":"publisher","first-page":"21289","DOI":"10.1002\/anie.202109326","article-title":"Design, Synthesis and Hydrogen Bonding of B3N6-[4]Triangulene","volume":"60","author":"Zhao","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210083794400_cit47","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202210386","article-title":"Solution-Phase Synthesis and Isolation\nof an Aza-Triangulene and Its Cation in Crystalline Form","volume":"61","author":"Wei","year":"2022","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210083794400_cit48","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202302714","article-title":"A Kinetically Stabilized Nitrogen-Doped Triangulene\nCation: Stable and NIR Fluorescent Diradical Cation with Triplet Ground\nState","volume":"62","author":"Arikawa","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210083794400_cit49","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-026-69048-1","article-title":"Solution-Synthesized\nStable Triaza[4]Triangulene Triradical with a Quartet Ground State","volume":"17","author":"Bai","year":"2026","journal-title":"Nat. Commun."},{"key":"2026081210083794400_cit50","doi-asserted-by":"publisher","first-page":"42133","DOI":"10.1021\/jacs.5c17094","article-title":"A Persistent Open-Shell m-QDM-Type Diindenoanthracene\nDiradicaloid with a Large Diradical Character","volume":"147","author":"Huang","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026081210083794400_cit51","doi-asserted-by":"publisher","first-page":"2824","DOI":"10.1039\/c3cs60461f","article-title":"Cationic Triangulenes and Helicenes:\nSynthesis, Chemical Stability, Optical Properties and Extended Applications\nof These Unusual Dyes","volume":"43","author":"Bosson","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"2026081210083794400_cit52","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202304197","article-title":"Fused Triangulene Dimers: Facile Synthesis by Intramolecular Radical\u2013Radical\nCoupling and Application for Near-Infrared Lasers","volume":"62","author":"Shen","year":"2023","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026081210083794400_cit53","doi-asserted-by":"publisher","first-page":"7914","DOI":"10.1021\/acs.orglett.4c02886","article-title":"Synthesis of Polycyclic\nAromatic Compounds by Electrocyclization-Dehydrogenation of Diradicaloids","volume":"26","author":"Liu","year":"2024","journal-title":"Org. 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Am.\nChem. Soc."},{"key":"2026081210083794400_cit58","doi-asserted-by":"publisher","first-page":"3864","DOI":"10.1021\/ja0018015","article-title":"Perchlorophenalenyl\nRadical","volume":"123","author":"Koutentis","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"2026081210083794400_cit59","doi-asserted-by":"publisher","first-page":"2399","DOI":"10.1021\/jacs.5b13033","article-title":"Biphenalenylidene:\nIsolation and Characterization of the Reactive Intermediate on the\nDecomposition Pathway of Phenalenyl Radical","volume":"138","author":"Uchida","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"2026081210083794400_cit60","doi-asserted-by":"publisher","first-page":"18122","DOI":"10.1021\/jacs.5c04413","article-title":"Phenalenyl Chemistry\nRevisited: Stable and Bioactive Multisubstituted Phenalenyl Radicals\nSynthesized via a Protection\u2013Oxidation\u2013Protection Strategy","volume":"147","author":"Tian","year":"2025","journal-title":"J. Am. Chem. 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