A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki–Miyaura Cross-Coupling

Materials

Guanglei Li¹  Yu Otsuka¹  Takuya Matsumiya¹  Koji Yamada¹  Masashi Takahashi²  Jianye Li²  Toshiyuki Suzuki² 

[1] Division of Materials Science, Graduate School of Environmental Science, Hokkaido University, Sapporo 0860-0810, Japan;Laboratory of Animal Genetics and Reproduction, Graduate School of Agriculture, Hokkaido University, Sapporo 060-8589, Japan;

关键词: BODIPY;    near-infrared;    fluorescence;    cellular imaging;    Suzuki–Miyaura cross-coupling;   

DOI  :  10.3390/ma11081297

来源: DOAJ

【 摘 要 】

In this study, a series of new red and near-infrared (NIR) dyes derived from 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) were developed by introducing thiophene and its derivatives to the 3- and 5- positions of the dichloroBODIPY core. For the first time, cyclictriol boronates and N-methyliminodiacetic acid (MIDA) boronate were used as organoboron species to couple with 3,5-dichloroBODIPY via the one-step Suzuki–Miyaura cross-coupling. Six kinds of thieno-expended BODIPY dyes were synthesized in acceptable yields ranging from 31% to 79%. All six dyes showed different absorption and emission wavelengths spanning a wide range (c.a. 600–850 nm) in the red and NIR regions with relatively high quantum yields (19–85%). Cellular imaging of 8-(2,6-dimethylphenyl)-re3,5-di(2-thienyl)-BODIPY (dye 1) was conducted using bovine cumulus cells, and the fluorescence microscopy images indicated that the chromophore efficiently accumulated and was exclusively localized in the cytoplasm, suggesting it could be utilized as a subcellular probe. All six dyes were characterized using 1H-NMR and mass spectrometry.

【 授权许可】

Unknown