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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.

Author information

1
Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602 (Japan).

Abstract

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.

KEYWORDS:

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

PMID:
25740735
DOI:
10.1002/anie.201500229
[Indexed for MEDLINE]

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