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

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 calorimetric 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, F-19 NMR spectra and H-1 NMR spectra titration experiments. (C) 2013 Elsevier Ltd. All rights reserved.