A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes,Angewandte Chemie International Edition

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A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2020-11-27 , DOI: 10.1002/anie.202012764
Hikaru Yanai ₁ , Shoki Hoshikawa ₁ , Yukiko Moriiwa ₁ , Atsushi Shoji ₁ , Akio Yanagida ₁ , Takashi Matsumoto ₁

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Installation of a carbanionic substituent, that is strongly stabilized by two (trifluoromethyl)sulfonyl (Tf=SO₂CF₃) groups, into several fluorescence dyes including boron‐dipyrromethenes (BODIPYs), fluoresceins, and aminocoumarins has been achieved by the 2,2‐bis(triflyl)ethylation reaction of the dye frameworks with highly electrophilic Tf₂C=CH₂, followed by neutralization with NaHCO₃. Despite the contradiction between water solubility and lipophilicity, the carbanion‐decorated dyes thus obtained showed significant enhancement of not only water solubility but also lipophilicity. This work clearly demonstrates that the fluorinated, highly stabilized carbanionic substituent is a new option for controlling the macroscopic property of chemical materials.

中文翻译：

含氟碳负离子取代基，可改善荧光染料的水溶性和亲脂性

2,2已成功实现了将由两个（三氟甲基）磺酰基（Tf = SO ₂ CF ₃）基团牢固稳定的碳负离子取代基安装到几种荧光染料中，包括硼二吡咯烷酮（BODIPYs），荧光素和氨基香豆素。带有高亲电性的Tf ₂ C = CH ₂的染料骨架发生双（三氟乙）乙基化反应，然后用NaHCO ₃中和。尽管水溶性和亲脂性之间存在矛盾，但如此获得的碳负离子修饰的染料不仅水溶性显着提高，而且亲脂性也显着提高。这项工作清楚地表明，氟化的高度稳定的碳负离子取代基是控制化学材料宏观性能的新选择。

更新日期：2020-11-27

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