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

作　　者：WANG Chao XIE Fang SUTHIWANGCHAROEN Nisaraporn SUN Jian WANG Qian 

机构地区：[1]Natural Products Center,Chengdu Institute of Biology,Chinese Academy of Sciences,Chengdu 610041,China [2]Department of Chemistry and Biochemistry,University of South Carolina,Columbia,SC 29208,USA

出　　处：《Science China Chemistry》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)

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.

关 键 词：CuAAC reaction FLUOROGENIC BODIPY dye cell imaging fluorescent probe 

分 类 号：O626[理学—有机化学] Q577[理学—化学]