Communication

A Colorimetric and Ratiometric Fluorescent Chemosensor with Three Emission Changes: Fluoride Ion Sensing by a Triarylborane– Porphyrin Conjugate†

  1. Yohei Kubo1,
  2. Masashi Yamamoto Dr.1,
  3. Masato Ikeda Dr.1,
  4. Masayuki Takeuchi Dr.1,
  5. Seiji Shinkai Prof.1,
  6. Shigehiro Yamaguchi Dr.2,
  7. Kohei Tamao Prof.2

Article first published online: 8 MAY 2003

DOI: 10.1002/anie.200250788

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 42, Issue 18, pages 2036–2040, May 9, 2003

Additional Information

How to Cite

Kubo, Y., Yamamoto, M., Ikeda, M., Takeuchi, M., Shinkai, S., Yamaguchi, S. and Tamao, K. (2003), A Colorimetric and Ratiometric Fluorescent Chemosensor with Three Emission Changes: Fluoride Ion Sensing by a Triarylborane– Porphyrin Conjugate. Angewandte Chemie International Edition, 42: 2036–2040. doi: 10.1002/anie.200250788

Author Information

  1. 1

    Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan, Fax: (+81) 92-642-3611

  2. 2

    Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan

  1. †

    Y.K. and M.Y contributed equally to this work. We thank Dr. Midori Watanabe and Ms. Hongyue Li at Kyushu University for 1H NMR measurements. M.T. and Y.K. thank prof. H. Yonemura for helpful discussions. M.I. thanks the JSPS Research Fellowship for Young Scientists for financial support. This work was partially supported by a grant-in-aid for COE research (“Design and Control of Advanced Molecular Assembly Systems”) from the Ministry of Education, Science, and Culture, Japan (no. 08CE2005).

Publication History

  1. Issue published online: 8 MAY 2003
  2. Article first published online: 8 MAY 2003
  3. Manuscript Received: 17 DEC 2002

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Keywords:

  • fluorescent probes;
  • fluorides;
  • molecular recognition;
  • porphyrinoids;
  • sensors

Graphical Abstract

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Perturbation in the energy-transfer pathway and of the π conjugation between the chromophores in a triarylborane–porphyrin conjugate on coordination of a fluoride ion to the boron center is assumed to account for the observation of the three emission bands (at 356, 670, and 692 nm). The system also displays a colorimetric (purple to green, see picture, and red to bluish emission) response to fluoride ions.

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