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The difficulty in rational development of triplet dyes increases exponentially as the absorption wavelength shifts deeper into the NIR range. Although classical H\u2010\/J\u2010typed packing of NIR dyes has the potential to enhance intersystem crossing (ISC) compared with that in single\u2010chromophore dyes, the triplet state quantum yields remain limited in such strategy. Herein, proximal oblique\u2010packed (V\u2010shaped) heptamethine cyanines (\n                    <jats:bold>SZ780<\/jats:bold>\n                    ) through spiro\u2010connection were achieved. Multi\u2010channel ultrafast ISC were direct observed in\n                    <jats:bold>SZ780<\/jats:bold>\n                    and a record high ISC rate constant (up to ~10\n                    <jats:sup>11<\/jats:sup>\n                    \u2005s\n                    <jats:sup>\u22121<\/jats:sup>\n                    ) is registered among all the reported NIR triplet dyes.\n                    <jats:bold>SZ780<\/jats:bold>\n                    exhibits a triplet state quantum yield of 18.9\u2009% upon excitation at 750\u2005nm, which is almost an order of magnitude higher than that of the monomer (\n                    <jats:bold>IR780<\/jats:bold>\n                    , 2.1\u2009%) and nearly threefold increase compared to that of the H\u2010packed dimer (\n                    <jats:bold>SC780<\/jats:bold>\n                    ) (6.7\u2009%). Moreover,\n                    <jats:bold>SZ780<\/jats:bold>\n                    efficiently generates singlet oxygen under 808\u2005nm light irradiation, inducing cancer cell apoptosis in vivo. These findings demonstrate that constructing V\u2010aggregated dyes system by spiro\u2010connection offers a powerful approach for the design of high\u2010performance NIR triplet sensitizers.\n                  <\/jats:p>","DOI":"10.1002\/anie.202425422","type":"journal-article","created":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T22:29:06Z","timestamp":1736893746000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Proximal Oblique\u2010Packing of Heptamethine Cyanines through Spiro\u2010Connection Boosts Triplet State Generation in Near\u2010Infrared"],"prefix":"10.1002","volume":"64","author":[{"given":"Xueli","family":"Wang","sequence":"first","affiliation":[{"name":"State Key Laboratory of Precision Spectroscopy East China Normal University  Shanghai 200241 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jie","family":"Zhou","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Precision Spectroscopy East China Normal University  Shanghai 200241 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mingkang","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioreactor Engineering Shanghai Key Laboratory of Chemical Biology School of Pharmacy East China University of Science and Technology  Shanghai 200237 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuze","family":"Wang","sequence":"additional","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University  Shanghai 200241 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhetao","family":"Shen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Precision Spectroscopy East China Normal University  Shanghai 200241 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haitao","family":"Sun","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Precision Spectroscopy East China Normal University  Shanghai 200241 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhubin","family":"Hu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Precision Spectroscopy East China Normal University  Shanghai 200241 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiao","family":"Luo","sequence":"additional","affiliation":[{"name":"Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development School of Chemistry and Molecular Engineering East China Normal University  Shanghai 200241 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Youjun","family":"Yang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Bioreactor Engineering Shanghai Key Laboratory of Chemical Biology School of Pharmacy East China University of Science and Technology  Shanghai 200237 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0652-1379","authenticated-orcid":false,"given":"Jinquan","family":"Chen","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Precision Spectroscopy East China Normal University  Shanghai 200241 China"},{"name":"Collaborative Innovation Center of Extreme Optics Shanxi University  Taiyuan, Shanxi 030006 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,1,22]]},"reference":[{"key":"e_1_2_8_1_1","unstructured":"\u00a0"},{"key":"e_1_2_8_2_2","doi-asserted-by":"publisher","DOI":"10.1038\/263443a0"},{"key":"e_1_2_8_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar000084g"},{"key":"e_1_2_8_4_1","unstructured":"\u00a0"},{"key":"e_1_2_8_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.0c00948"},{"key":"e_1_2_8_6_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-024-01446-8"},{"key":"e_1_2_8_7_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-022-29981-3"},{"key":"e_1_2_8_8_1","unstructured":"\u00a0"},{"key":"e_1_2_8_9_2","author":"Pham T. 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