Reaction-Based Sensing of Fluoride Ions Using Built-In Triggers for Intramolecular Charge Transfer and Photoinduced Electron Transfer

Özgür Altan Bozdemir, Fazlı Sözmen, Onur Büyükçakır, Ruslan Guliyev, Yusuf Çakmak, Engin U. Akkaya

Organic Letters · 2010 · 195 citations · 40 references

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Abstract

Two Bodipy derivatives with silyl-protected phenolic functionalities signal fluoride concentrations both in solution and in a poly(methyl methacrylate) matrix. The exact location of the "nascent" phenolate group is important. If it is at the meso position, photoinduced electron transfer is triggered; however, if it is in full conjugation via a styryl moiety to the Bodipy core, strong intramolecular charge transfer is triggered, resulting in a large red shift in the absorbance peak. In either case, a selective methodology for fluoride sensing is the invariable result.

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