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J Org Chem. 2013 Jun 21;78(12):6121-30. doi: 10.1021/jo400783x. Epub 2013 Jun 7.

Coumarin- and rhodamine-fused deep red fluorescent dyes: synthesis, photophysical properties, and bioimaging in vitro.

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Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.


A series of deep red fluorescent dyes (CR1 to CR3) was developed via introduction of a coumarin moiety into the rhodamine molecular skeleton. The novel dyes possessed the individual advantages of coumarin and rhodamine derivatives, and the emission wavelength was extended to the deep red region (>650 nm) due to the extension of fused-ring conjugate structure simultaneously. To illustrate its value, we designed and conveniently synthesized a series of novel deep red bioimaging dyes (CR1E to CR3E) by esterification of CR1 to CR3, which could selectively stain mitochondria. They were superior to the MitoTrackers for mitochondrial staining in terms of large Stokes shift, excellent contrast for imaging, high photostability, and low cytotoxicity. Furthermore, the fluorescence of the coumarin moiety and rhodamine-like fluorophore could be switched like classical rhodamine. Thus, they could be used as an effective platform in constructing fluorescence sensors. Based on this fact, we constructed a novel ratiometric sensor (CR1S) for Hg(2+) with good selectivity that could be successfully applied to the imaging of Hg(2+) in living A549 cells. This design strategy is straightforward and adaptable to various deep red dyes and sensing platforms by simply introducing different fluorophores.

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