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Tuning the optical properties of BODIPY dye through Cu(Ⅰ) catalyzed azide-alkyne cycloaddition(CuAAC) reaction 被引量:1

Tuning the optical properties of BODIPY dye through Cu(Ⅰ) catalyzed azide-alkyne cycloaddition(CuAAC) reaction
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摘要 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. 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.
出处 《Science China Chemistry》 SCIE EI CAS 2012年第1期125-130,共6页 中国科学(化学英文版)
基金 supported by the Alfred P. Sloan Scholarship, Camille Dreyfus Teacher Scholar Award,the W.M.Keck Foundation,and the Colon Cancer Center of University of South Carolina support from the National Natural Science Foundation of China(91013006)
关键词 环加成反应 肾上腺素 荧光染料 叠氮 光学特性 催化 荧光量子产率 调整 CuAAC reaction fluorogenic BODIPY dye cell imaging fluorescent probe
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