A new diketopyrrolopyrrole (DPP) derivative bearing boronate group as fluorescent probe for fluoride ion

• A novel diketopyrrolopyrrole (DPP) derivative was synthesized under mild conditions.
• It was a fluorescent probe for fluoride ion with high sensitivity and selectivity.
• The recognition mechanism was attributed to unique fluoride–boron interaction.
• It could play an important role in the synthesis of organic optoelectronic materials.

A new diketopyrrolopyrrole (DPP) derivative bearing pinacol boronate group has been synthesized via Suzuki–Miyaura reaction under mild conditions in good yield. The product could act as a colorimetric and ratiometric fluorescent probe for fluoride ion with high sensitivity and selectivity. The recognition mechanism was attributed to unique fluoride–boron interaction, which blocked the charge transfer (CT) between DPP chromophore and the empty p orbitals of boron atoms, and proved by the fluorescence spectra, 19F NMR spectra and 1H NMR spectra titration experiments.