A tripodal-based hexaurea receptor appended with m-nitrophenyl groups has been studied for halide binding by proton NMR, UV-Vis titrations, and high level density functional theory (DFT) calculations. As demonstrated by experimental and computational results, the receptor effectively binds a halide ion in a 1:2 binding mode showing the binding strength in the order of fluoride &gt; chloride &gt; bromide &gt; iodide. The strongest affinity for fluorides is attributed to the best fit of two fluoride anions within the host's cavity. This is also supported by DFT calculations, showing that each anion is stabilized by six NH…F bonds - one at the inner cleft and other at the outer cleft. The receptor was further investigated for its biocompatibility on HeLa cells, showing excellent cell viability.

Non-covalent interactions of halides with a nitrophenyl-functionalized hexaurea receptor

256th National Meeting (2018)

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