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首页> 外文期刊>Chemistry: A European journal >Intensely fluorescent azobenzenes: Synthesis, crystal structures, effects of substituents, and application to fluorescent vital stain
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Intensely fluorescent azobenzenes: Synthesis, crystal structures, effects of substituents, and application to fluorescent vital stain

机译：强烈的荧光偶氮苯：合成，晶体结构，取代基的作用以及在荧光生物染色剂中的应用

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摘要

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 4position have been synthesized. The 4bromo 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.
机译：合成了在4'位带有氢，甲氧基，二甲基氨基，三氟甲基，氟，正丁基和叔丁基二甲基甲硅烷氧基或在4位带有甲氧基和溴基的2- [双（五氟苯基）硼基]偶氮苯。通过钯催化的反应，将2-硼基-4-溴偶氮苯衍生物的4-溴基转化为苯基和二苯基氨基。已经使用UV / Vis和荧光光谱研究了吸收和荧光性质。 2-硼基偶氮苯发出强烈的绿色，黄色和橙色荧光，与通常的偶氮苯荧光形成鲜明对比。迄今为止，在偶氮苯中报道的4'-甲硅烷氧基衍生物的荧光量子产率最高（0.90）。通过研究取代基对弛豫过程的影响以及DFT和TD-DFT计算，阐明了取代基与荧光性质之间的相关性。发现在4'-位的给电子基团对于强发射很重要。还通过显微注射到非洲爪蟾胚胎中研究了荧光偶氮苯作为荧光活体染色剂在活体组织可视化中的应用，表明这些化合物对胚胎无毒。

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