Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 54, Pages 14506-14512Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201802875
Keywords
dyes; pigments; fluorescent probes; imaging agents; near-infrared fluorophores; phosphorus
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Funding
- National Natural Science Foundation of China [21205135, 21602250, 21705049]
- Shanghai Pujiang program [17PJ1402000]
- Innovation Program of Shanghai Municipal Education Commission [201701070005E00020]
- Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
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Replacement of the bridging oxygen atom in rhodamine with phosphorus is one of the most efficient ways for bright near-infrared (NIR) fluorophores with wavelengths over 700 nm. However, the organophosphorus bridge is more versatile than just being a spectrum tuner, it is also a profound solubility booster and photostability enhancer, as proved by a series of phosphorus-substituted rhodamines (PRBs). A unique bridge-caging strategy for efficiently manipulating fluorescence has further been innovated in example PRB2. Consistent with theoretical calculations, the formation of organophosphinate by a caging group as a fluorescence-controller locks the spirolactone into a colorless and nonfluorescent form, whereas decaging, a process induced by a specific stimulus, results in a ring-opened form, which yields strong fluorescence. The bridge-caging strategy is feasible for the modular development of NIR probes. Efficient in vivo imaging of photoillumination, hydrogen peroxide, and enzyme have been achieved on the PRB2 scaffold as a photoactivatable fluorophore, PRB2-h nu; fluorescent indicator, PRB2-H2O2; and fluorogenic enzyme substrate, PRB2-NTR, respectively.
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