Chemodosimeter approach: Selective detection of fluoride ion using a diketopyrrolopyrrole derivative

•Diketopyrrolopyrrole with trimethylsilyl groups has been designed and synthesized as fluoride chemodosimeter.•The probe is highly selective, sensitive, and fast chemodosimeter for fluoride ion.•Addition of fluoride to probe solution resulted in blue shift of absorption and fluorescence spectra.•Density functional calculations (DFT) support the experimental results.•The probe has the capability to detect fluoride in solution as well as in solid state.

A diketopyrrolopyrrole derivative was synthesized and designed with two trimethylsilyl groups to allow for sensitive, selective and fast recognition of fluoride ions by using a chemodosimeter approach. The probe exhibited a blue shift in the absorption and emission spectra in the presence of fluoride ions due to deprotection of the electron donating trimethylsilyl groups in the probe. UV–vis absorption, fluorescence, density functional theory and cyclic voltammetry studies indicated fluoride triggered cleavage of the Si–C bond resulting in the blue spectral shift.

Graphical abstractA fluoride ion triggered Si–C bond cleavage in a diketopyrrolopyrrole derivative containing trimethylsilyl groups. The probe exhibits a blue shift in the absorption and emission spectra in the presence of fluoride ions due to deprotection of the trimethylsilyl groups.Figure optionsDownload full-size imageDownload as PowerPoint slide