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Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction

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Abstract

Borondipyrromethenes (BODIPY) are a class of fluorescent dyes whose fluorescence quantum yields are generally high and independent of the solvent. In this paper, we report the synthesis of a new type of BODIPY compound that carries an azido group on the 3-position of the pyrrole core. The azido group quenches the fluorescence of the dye due to its weak electron-donating effect. The fluorescence of the BODIPY dye can be switched on after reacting with alkynes via a Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction. We further demonstrate that this azido-BODIPY compound can be used in the cell imaging applications.

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Authors and Affiliations

  1. Natural Products Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041, China

    Chao Wang & Jian Sun

  2. Department of Chemistry and Biochemistry, University of South Carolina, Columbia, SC, 29208, USA

    Fang Xie, Nisaraporn Suthiwangcharoen & Qian Wang

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  1. Chao Wang
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  2. Fang Xie
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  3. Nisaraporn Suthiwangcharoen
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  4. Jian Sun
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Correspondence to Jian Sun or Qian Wang.

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Wang, C., Xie, F., Suthiwangcharoen, N. et al. Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Sci. China Chem. 55, 125–130 (2012). https://doi.org/10.1007/s11426-011-4452-2

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  • DOI: https://doi.org/10.1007/s11426-011-4452-2

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