Fluorescent pH‐Responsive Probes Based on Water‐Soluble Boron‐Dipyrromethene (BODIPY) Derivatives, Featuring Long‐Wavelength Emission,Chemistry - A European Journal

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Fluorescent pH‐Responsive Probes Based on Water‐Soluble Boron‐Dipyrromethene (BODIPY) Derivatives, Featuring Long‐Wavelength Emission
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2018-07-03 , DOI: 10.1002/chem.201801540
Alexandra Sutter ₁ , Mourad Elhabiri ₂ , Gilles Ulrich ₁

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We describe here the synthesis of water‐soluble red/NIR‐emissive, boron‐dipyrromethene (BODIPY) derivatives displaying optical (absorption and emission) responses in pH range of 4–8. Substitution close to the tertiary aniline or the phenol subunits selected as the proton‐sensitive sites allowed us to finely tune the pH ranges. Furthermore, the introduction of sulfobetaine functions at the boron centre of these pH‐responsive BODIPYs afforded valuable fluorescent dyes in the red/NIR region in aqueous media, for which the steric hindrance and electrostatic repulsions prevent their non‐emissive aggregation. All the absorption and emission studies, as well as the protonation properties were investigated in aqueous, ethanolic and saline solutions (mimicking physiological conditions). Interestingly, the systems present a fluorescent ratiometric protonation response in EtOH, but the non‐protonated form is almost a non‐fluorescent species under quasi‐physiological conditions (saline aqueous solutions) due to the fading of the emissive character of the low‐lying charge‐transfer transition in the presence of a supporting electrolyte.

中文翻译：

基于水溶性硼二吡咯亚甲基（BODIPY）衍生物的荧光pH响应探针，具有长波长发射

我们在这里描述了水溶性红色/ NIR发射性的硼-二吡咯亚甲基（BODIPY）衍生物的合成，在4-8的pH范围内表现出光学（吸收和发射）响应。接近于叔苯胺或被选为质子敏感位点的酚亚基的取代基使我们能够精细调节pH范围。此外，在这些pH响应BODIPY硼中心引入磺基甜菜碱功能，在水性介质的红色/近红外区域提供了有价值的荧光染料，其空间位阻和静电排斥阻止了它们的非发射性聚集。在水溶液，乙醇溶液和盐溶液中（模拟生理条件）研究了所有吸收和发射研究以及质子化性质。有趣的是，

更新日期：2018-07-03

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