In this work four new tripodal tris(halopyridinium) receptors containing potentially halogen

bonding groups were prepared. The ability of the receptors to bind anions in competitive

CD₃CN/d₆-DMSO was studied using ¹H NMR titration experiments, which revealed that the

receptors bind chloride anions more strongly than more basic acetate or other halide ions.

The solid state self–assembly of the tripodal receptors with halide anions was investigated by

X-ray crystallography. The nature of the structures was dependent on the choice of halide

anion, as well as the crystallisation solvent. Halogen bond lengths as short as 80% of the sum

of the van der Waals radii were observed, which is shorter than any halogen bonds involving

halopyridinium receptors in the Cambridge Structural Database.

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