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Mono- and Di(dimethylamino)styryl-Substituted Borondipyrromethene and Borondiindomethene Dyes with Intense Near-Infrared Fluorescence

  1. Yan-Hong Yu1,
  2. Ana B. Descalzo Dr.2,
  3. Zhen Shen Prof.1,
  4. Holger Röhr2,3,
  5. Quan Liu1,
  6. Yan-Wei Wang1,
  7. Monika Spieles2,
  8. Yi-Zhi Li Prof.1,
  9. Knut Rurack Dr.2,
  10. Xiao-Zeng You Prof.1

Article first published online: 10 JUL 2006

DOI: 10.1002/asia.200600042

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 1, Issue 1-2, pages 176–187, July 17, 2006

Additional Information

How to Cite

Yu, Y.-H., Descalzo, Ana B., Shen, Z., Röhr, H., Liu, Q., Wang, Y.-W., Spieles, M., Li, Y.-Z., Rurack, K. and You, X.-Z. (2006), Mono- and Di(dimethylamino)styryl-Substituted Borondipyrromethene and Borondiindomethene Dyes with Intense Near-Infrared Fluorescence. Chem. Asian J., 1: 176–187. doi: 10.1002/asia.200600042

Author Information

  1. 1

    Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, China, Fax: (+86) 25-8331-4502

  2. 2

    Div. I.5, Bundesanstalt für Materialforschung und -prüfung (BAM), Richard Willstätter Strasse 11, 12489 Berlin, Germany, Fax: (+49) 30-8104-5005

  3. 3

    Associated with: Fachbereich Biologie, Chemie, Pharmazie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany

Publication History

  1. Issue published online: 10 JUL 2006
  2. Article first published online: 10 JUL 2006
  3. Manuscript Received: 26 FEB 2006

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Keywords:

  • borondipyrromethene;
  • dyes;
  • fluorescence;
  • indicators;
  • protonation

Abstract

Four novel borondipyrromethene (BDP) and -diindomethene (BDI) dyes with one or two (dimethylamino)styryl extensions at the chromophore were synthesized and spectroscopically investigated. An X-ray crystal structure shows that the extended auxochrome is virtually planar. All dyes thus display intense red/near infrared (NIR) absorption and emission. The (dimethylamino)styryl group induces a charge-transfer character that entails bright solvatochromic fluorescence, which is only quenched with increasing solvent polarity according to the energy-gap law. The dye with an additional dimethylanilino group at the meso position of BDP shows a remarkable switching of lipophilicity by protonation. Two dyes with an 8-hydroxyquinoline ligand at the meso position display quenched emission in the presence of Hg2+ or Al3+ owing to electron transfer from the excited BDP to the complexed receptor. The BDI dye presents a pH indicator with bright fluorescence and extremely low fluorescence anisotropy.

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