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Angew Chem Int Ed Engl. 2015 Apr 7;54(15):4539-43. doi: 10.1002/anie.201500229. Epub 2015 Mar 4.

Environment-sensitive fluorescent probe: a benzophosphole oxide with an electron-donating substituent.

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Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602 (Japan).


Electron-donating aryl groups were attached to electron-accepting benzophosphole skeletons. Among several derivatives thus prepared, one benzophosphole oxide was particularly interesting, as it retained high fluorescence quantum yields even in polar and protic solvents. This phosphole-based compound exhibited a drastic color change of its fluorescence spectrum as a function of the solvent polarity, while the absorption spectra remained virtually unchanged. Capitalizing on these features, this phosphole-based compound was used to stain adipocytes, in which the polarity of subcellular compartments could then be discriminated on the basis of the color change of the fluorescence emission.


fluorescent probes; imaging agents; phosphole; phosphorus heterocycles; solvatochromism

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