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Carbonyl groups were found to increase the reduction potential of the BODIPY core by 0.15\u20130.4\u2005eV compared to regular alkyl\u2010substituted BODIPYs. These compounds exhibited efficient intramolecular charge separation and triplet state formation through the spin\u2010orbit charge transfer intersystem crossing (SOCT\u2010ISC) process, achieving singlet oxygen quantum yields of up to 92\u2009%, depending on the solvent polarity. Notably, the fluorescence and singlet oxygen generation of <jats:bold>BDP\u2010DA<\/jats:bold>s were found to depend on the ionization state of the carboxylic groups. Time\u2010resolved fluorescence measurements revealed that complexation of <jats:bold>BDP\u2010DA<\/jats:bold>s with bovine serum albumine (BSA) significantly extended their excited state lifetimes. Fluorescence lifetime imaging microscopy (FLIM) studies of human colorectal carcinoma (HCT116) cells and pig small intestinal organoids (enteroids) provided insights into subcellular localization. The diacid with 2,4\u2010dimethoxyphenyl group at the <jats:italic>meso<\/jats:italic>\u2010position (<jats:bold>DA1<\/jats:bold>) displayed longer lifetimes in lipid\u2010droplet\u2010like structures and shorter lifetimes in cytoplasmic regions. The diacid containing a <jats:italic>meso<\/jats:italic>\u2010anthracenyl group (<jats:bold>DA2<\/jats:bold>) formed \u2032islands\u2019 in cell monolayers, exhibiting a distinct lifetime gradient from the periphery to the center. These results highlight the potential of donor\u2010acceptor BODIPYs as fluorescent probes for biological imaging, particularly in revealing subtle differences in cellular environments.<\/jats:p>","DOI":"10.1002\/chem.202404188","type":"journal-article","created":{"date-parts":[[2024,12,31]],"date-time":"2024-12-31T14:30:32Z","timestamp":1735655432000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Optoelectronic Properties and Fluorescence Lifetime Imaging Application of Donor\u2010Acceptor Dyads Derived From 2,6\u2010DicarboxyBODIPY"],"prefix":"10.1002","volume":"31","author":[{"given":"Aimee","family":"Sheehan","sequence":"first","affiliation":[{"name":"School of Chemical and Biopharmaceutical Sciences Technological University Dublin City Campus, Grangegorman  Dublin 7 Ireland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina A.","family":"Okkelman","sequence":"additional","affiliation":[{"name":"Tissue Engineering and Biomaterials Group Department of Human Structure and Repair Faculty of Medicine and Health Sciences Ghent University The Core, C. 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