Intensely Fluorescent Azobenzenes: Synthesis, Crystal Structures, Effects of Substituents, and Application to Fluorescent Vital Stain
| Autor: | Yoshino, Junro, Furuta, Akiko, Kambe, Tetsuya, Itoi, Hiroaki, Kano, Naokazu, Kawashima, Takayuki, Ito, Yuzuru, Asashima, Makoto |
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| Jazyk: | angličtina |
| Rok vydání: | 2010 |
| Předmět: |
Embryo
Nonmammalian Microinjections Xenopus Substituent Quantum yield Crystal structure Crystallography X-Ray Photochemistry Fluorescence Catalysis Fluorescence spectroscopy Structure-Activity Relationship chemistry.chemical_compound Animals Boranes Fluorescent Dyes Trifluoromethyl Molecular Structure Organic Chemistry General Chemistry Spectrometry Fluorescence Models Chemical Azobenzene chemistry Vital stain Azo Compounds Palladium |
| Zdroj: | Chemistry-a European Journal. 16(No. 17):5026-5035 |
| ISSN: | 0947-6539 |
| Popis: | 2-[Bis(pentafluorophenyl)boryl]azobenzenes bearing hydrogen, methoxy, dimethylamino, trifluoromethyl, fluoro, n-butyl, and tert-butyldimethylsiloxy groups at the 4'-position or methoxy and bromo groups at the 4-position have been synthesized. The 4-bromo group of the 2-boryl-4-bromoazobenzene derivative was converted to phenyl and diphenylamino groups by palladium-catalyzed reactions. The absorption and fluorescence properties have been investigated using UV/Vis and fluorescence spectroscopy. The 2-borylazobenzenes emitted an intense green, yellow, and orange fluorescence, in marked contrast to the usual azobenzene fluorescence. The 4'-siloxy derivative showed the highest fluorescence quantum yield (0.90) among those reported for azobenzenes to date. The correlation between the substituent and the fluorescence properties was elucidated by studying the effect of the substituent on the relaxation process and from DFT and TD-DFT calculations. An electron-donating group at the 4'-position was found to be important for an intense emission. Application of fluorescent azobenzenes as a fluorescent vital stain for the visualization of living tissues was also investigated by microinjection into Xenopus embryos, suggesting these compounds are nontoxic towards embryos. |
| Databáze: | OpenAIRE |
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