Abstract
The isolation and structural characterisation of two ionic complexes (S)-3 and(S)-4 based on fluoride ion-mediated deprotonation of 1,1′-bi-2-naphthol (BINOL) derivatives (S)-1 and (S)-2 have been carried out for the first time. X-ray crystallographic study showed that the deprotonated forms (S)-3 and (S)-4 adopt remarkably different molecular geometries, bond parameters as well as molecular packing modes from their neutral analogs, in agreement with their significant fluorescence changes upon the addition of fluoride ion, giving insights into the actual mechanism of fluoride ion fluorescence sensing. The deprotonation–protonation processes in two BINOL derivatives were also investigated by both fluorescence measurements and X-ray structural analyses. Such chiral basic compounds can be promising organocatalysts for asymmetric reactions.
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