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

被引：0
|
作者：
Chao Wang
Fang Xie
Nisaraporn Suthiwangcharoen
Jian Sun
Qian Wang
机构：
[1] Chinese Academy of Sciences,Natural Products Center, Chengdu Institute of Biology
[2] University of South Carolina,Department of Chemistry and Biochemistry
来源：
Science China Chemistry | 2012年 / 55卷
关键词：
CuAAC reaction; fluorogenic; BODIPY dye; cell imaging; fluorescent probe;
D O I：
暂无
中图分类号：
学科分类号：
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.
引用
收藏
页码：125 / 130
页数：5
相关论文
共 50 条
  • [1] Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction
    Wang Chao
    Xie Fang
    Suthiwangcharoen, Nisaraporn
    Sun Jian
    Wang Qian
    SCIENCE CHINA-CHEMISTRY, 2012, 55 (01) : 125 - 130
  • [2] Tuning the optical properties of BODIPY dye through Cu(I) catalyzed azide-alkyne cycloaddition(CuAAC) reaction
    SUTHIWANGCHAROEN Nisaraporn
    中国科学:化学, 2012, 42 (02) : 231 - 232
  • [3] Tuning the optical properties of BODIPY dye through Cu(Ⅰ) catalyzed azide-alkyne cycloaddition(CuAAC) reaction
    SUTHIWANGCHAROEN Nisaraporn
    ScienceChina(Chemistry), 2012, 55 (01) : 125 - 130
  • [4] Photoinitiated Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) based networks
    Baranek, Austin
    Song, Han Byul
    McBride, Matthew
    Finnegan, Patricia
    Gong, Tao
    Bowman, Christopher
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [5] Photoinitiated copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) reaction for conductive network synthesis
    El-Zaatari, Bassil
    Tibbits, Andrew
    Kloxin, Christopher
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [6] Photopolymerization Reactions Using the Photoinitiated Copper (I)-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) Reaction
    Gong, Tao
    Adzima, Brian J.
    Baker, Noah H.
    Bowman, Christopher N.
    ADVANCED MATERIALS, 2013, 25 (14) : 2024 - 2028
  • [7] Mechanistic investigation of Cu(I) catalyzed azide-alkyne cycloaddition reaction.
    Rodionov, VO
    Fokin, VV
    Finn, MG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U583 - U583
  • [8] Development and Applications of the Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) as a Bioorthogonal Reaction
    Li, Li
    Zhang, Zhiyuan
    MOLECULES, 2016, 21 (10)
  • [9] Cu-catalyzed azide-alkyne cycloaddition
    Meldal, Morten
    Tornoe, Christian Wenzel
    CHEMICAL REVIEWS, 2008, 108 (08) : 2952 - 3015
  • [10] Simultaneous copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) and living radical polymerization
    Geng, Jin
    Lindqvist, Josefina
    Mantovani, Giuseppe
    Haddleton, David M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) : 4180 - 4183
12345