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By fine\u2010tuning the substitution of electron\u2010donating pyrenes, the complex interplay among different excited\u2010state decay channels and the overall impact of solvents on these decay channels were uncovered. Placing pyrene, for example, at the aromatic ketones resulted in a profound solvatochromism in the form of a bright charge\u2010transfer (CT) emission spanning from yellow to red\u2010NIR. In contrast, a dark non\u2010emissive CT was noted upon pyrene substitution at the fluorenes. In apolar solvents, efficient triplet\u2010excited state generation was observed for all SFDBAOs. Either charge transfer was concluded to mediate the intersystem crossing (ISC) in the case of pyrene substitution or the El\u2010Sayed rule was applicable when lacking pyrene substitution as in the case of SFABAO. In polar solvents, charge separation is the sole decay upon pyrene substitution. Moreover, competition between ISC and CT lowered the triplet\u2010excited state generation in SFDBAO.<\/jats:p>","DOI":"10.1002\/anie.202313936","type":"journal-article","created":{"date-parts":[[2024,2,7]],"date-time":"2024-02-07T02:11:23Z","timestamp":1707271883000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":20,"title":["Tuning the Absorption, Fluorescence, Intramolecular Charge Transfer, and Intersystem Crossing in Spiro[fluorene]acridinone"],"prefix":"10.1002","volume":"63","author":[{"given":"Yifan","family":"Bo","sequence":"first","affiliation":[{"name":"Department of Chemistry and Pharmacy &amp; Interdisciplinary Center of Molecular Materials Friedrich-Alexander-Universit\u00e4t Erlangen-N\u00fcrnberg  Egerlandstrasse 3 91058 Erlangen Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"He","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory for Organic Electronics and Information Displays Institute of Advanced Materials (IAM) Center for Molecular Systems and Organic Devices (CMSOD) Nanjing University of Posts and Telecommunications  Wenyuan Road 9 Nanjing 210023 China"},{"name":"School of Materials Science and Engineering Anhui University  Jiulong Road 111 Hefei 230601 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yue","family":"Li","sequence":"additional","affiliation":[{"name":"Key Laboratory for Organic Electronics and Information Displays Institute of Advanced Materials (IAM) Center for Molecular Systems and Organic Devices (CMSOD) Nanjing University of Posts and Telecommunications  Wenyuan Road 9 Nanjing 210023 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yana","family":"Reva","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Pharmacy &amp; 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