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

Authors

  • Yan-Hong Yu,

    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
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  • Ana B. Descalzo Dr.,

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

    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
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  • Holger Röhr,

    1. Div. I.5, Bundesanstalt für Materialforschung und -prüfung (BAM), Richard Willstätter Strasse 11, 12489 Berlin, Germany, Fax: (+49) 30-8104-5005
    2. Associated with: Fachbereich Biologie, Chemie, Pharmazie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany
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  • Quan Liu,

    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
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  • Yan-Wei Wang,

    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
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  • Monika Spieles,

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

    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
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  • Knut Rurack Dr.,

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

    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
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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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