Abstract
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.
Highlights
A Straightforward Substitution Strategy to TuneGuanglei Li 1 , Yu Otsuka 1 , Takuya Matsumiya 1 , Toshiyuki Suzuki 2 , Jianye Li 2 , Masashi Takahashi 2,3 and Koji Yamada 1,4, *
Long-wavelength dyes, which absorb and emit light in the far-red and near-infrared (NIR) region, have found extensive applications in biology [1] as the spectra in the NIR region has many advantages, such as enhanced sensitivity owing to high contrast and low background noise, deep penetration in tissue, and less damage to organisms
Using cyclictriol boronates and N-methyliminodiacetic acid (MIDA) boronate as organoboron species, a set of red and NIR BODIPY dyes were synthesized (Figure 1) in acceptable yields ranging from 31% to 51% under mild reaction conditions, all of which exhibited relatively high quantum yields in the range of 0.19 to 0.85
Summary
Guanglei Li 1 , Yu Otsuka 1 , Takuya Matsumiya 1 , Toshiyuki Suzuki 2 , Jianye Li 2 , Masashi Takahashi 2,3 and Koji Yamada 1,4, *. Division of Materials Science, Faculty of Environmental Earth Science, Hokkaido University, Sapporo 0860-0810, Japan
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