Fluorescent pH Responsive Probes Based on Water Soluble BODIPY, Featuring Long Wavelength Emission

We describe here the synthesis of water soluble Red-NIR emissive BODIPY derivatives displaying optical (absorption and emission) responses in pH ranges of interest. Substitution effects close to the tertiary aniline or the phenol subunits selected as the proton sensitive sites allowed us to finely t...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-05
Main Authors: Ulrich, Gilles, Sutter, Alexandra, Elhabiri, Mourad
Format: Article
Language:English
Online Access:Get full text
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Summary:We describe here the synthesis of water soluble Red-NIR emissive BODIPY derivatives displaying optical (absorption and emission) responses in pH ranges of interest. Substitution effects close to the tertiary aniline or the phenol subunits selected as the proton sensitive sites allowed us to finely tune the pH ranges. Furthermore, 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 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 CT transition in the presence of a supporting electrolyte.
ISSN:1521-3765