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

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Title: A Straightforward Substitution Strategy to Tune BODIPY Dyes Spanning the Near-Infrared Region via Suzuki-Miyaura Cross-Coupling
Authors: Li, Guanglei Browse this author
Otsuka, Yu Browse this author
Matsumiya, Takuya Browse this author
Suzuki, Toshiyuki Browse this author
Li, Jianye Browse this author
Takahashi, Masashi Browse this author
Yamada, Koji Browse this author →KAKEN DB
Keywords: BODIPY
near-infrared
fluorescence
cellular imaging
Suzuki-Miyaura cross-coupling
Issue Date: Aug-2018
Publisher: MDPI
Journal Title: Materials
Volume: 11
Issue: 8
Start Page: 1297
Publisher DOI: 10.3390/ma11081297
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.
Rights: https://creativecommons.org/licenses/by/4.0/
Type: article
URI: http://hdl.handle.net/2115/71649
Appears in Collections:環境科学院・地球環境科学研究院 (Graduate School of Environmental Science / Faculty of Environmental Earth Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 山田 幸司

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