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Angewandte Chemie International Edition
Communication

Environment‐Sensitive Fluorescent Probe: A Benzophosphole Oxide with an Electron‐Donating Substituent*

Eriko Yamaguchi

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

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Chenguang Wang

Institute of Transformative Bio‐Molecules (WPI‐ITbM), Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Prof. Dr. Aiko Fukazawa

Corresponding Author

E-mail address:aiko@chem.nagoya‐u.ac.jp

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

Aiko Fukazawa, Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Tetsuya Higashiyama, Division of Biological Science, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Shigehiro Yamaguchi, Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Prof. Dr. Masayasu Taki

Institute of Transformative Bio‐Molecules (WPI‐ITbM), Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Dr. Yoshikatsu Sato

Institute of Transformative Bio‐Molecules (WPI‐ITbM), Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Taeko Sasaki

Division of Biological Science, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Dr. Minako Ueda

Institute of Transformative Bio‐Molecules (WPI‐ITbM), Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Prof. Dr. Narie Sasaki

Division of Biological Science, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Prof. Dr. Tetsuya Higashiyama

Corresponding Author

E-mail address:higashi@bio.nagoya‐u.ac.jp

Division of Biological Science, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Institute of Transformative Bio‐Molecules (WPI‐ITbM), Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Aiko Fukazawa, Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Tetsuya Higashiyama, Division of Biological Science, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Shigehiro Yamaguchi, Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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Prof. Dr. Shigehiro Yamaguchi

Corresponding Author

E-mail address:yamaguchi@chem.naogya‐u.ac.jp

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

Institute of Transformative Bio‐Molecules (WPI‐ITbM), Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Aiko Fukazawa, Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Tetsuya Higashiyama, Division of Biological Science, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

Shigehiro Yamaguchi, Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464‐8602 (Japan)

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First published: 04 March 2015
Cited by: 68
*

This work was supported by JST, CREST (S.Y.), a Grant‐in‐Aid for Scientific Research on Innovative Areas “Organic Synthesis based on Reaction Integration” (no. 2105) from MEXT (Japan) (A.F.), and the Japan Advanced Plant Science Network. E.Y. thanks the JSPS for a Research Fellowship for Young Scientists. ITbM is supported by the World Premier International Research Center (WPI) Initiative, 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.

Number of times cited: 68

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