一种用于提高荧光染料水溶性和亲脂性的氟化碳负离子取代基。
A Fluorinated Carbanionic Substituent for Improving Water Solubility and Lipophilicity of Fluorescent Dyes.
作者信息
Yanai Hikaru, Hoshikawa Shoki, Moriiwa Yukiko, Shoji Atsushi, Yanagida Akio, Matsumoto Takashi
机构信息
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
出版信息
Angew Chem Int Ed Engl. 2021 Mar 1;60(10):5168-5172. doi: 10.1002/anie.202012764. Epub 2021 Jan 21.
Installation of a carbanionic substituent, that is strongly stabilized by two (trifluoromethyl)sulfonyl (Tf=SO CF ) 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 Tf C=CH , followed by neutralization with NaHCO . 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.
通过染料骨架与高亲电性的三氟甲基磺酰基乙炔（Tf₂C=CH₂）进行2,2-双（三氟甲磺酰基）乙基化反应，随后用碳酸氢钠中和，已成功地将由两个（三氟甲基）磺酰基（Tf = SO₂CF₃）强烈稳定的碳负离子取代基引入到包括硼二吡咯亚甲基（BODIPY）、荧光素和氨基香豆素在内的几种荧光染料中。尽管水溶性和亲脂性之间存在矛盾，但由此获得的碳负离子修饰染料不仅水溶性显著增强，而且亲脂性也显著增强。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质的一种新选择。
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