Fluorescent pH-Responsive Probes Based on Water-Soluble Boron-Dipyrromethene (BODIPY) Derivatives, Featuring Long-Wavelength Emission - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2018

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

Résumé

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.

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CBM

Domaines

Chimie organique
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Dates et versions

hal-02167616 , version 1 (27-06-2019)

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A Sutter, Mourad Elhabiri, Gilles Ulrich. Fluorescent pH-Responsive Probes Based on Water-Soluble Boron-Dipyrromethene (BODIPY) Derivatives, Featuring Long-Wavelength Emission. Chemistry - A European Journal, 2018, 24 (43), pp.11119-11130. ⟨10.1002/chem.201801540⟩. ⟨hal-02167616⟩
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