To design a macrocycle that optimises size complementarity and solvation discrimination, we replaced the two pentafluorophenyl substituents of 1 with a linker of varying lengths. To minimise the build up of ring strain upon cyclisation, we surveyed available procedures in the literature for synthesising a macrocyclic meta-bis-triazolobenzene motif, which revealed that the smallest reported macrocycle had a minimum of 15 atoms in the linker between the triazole N atoms. Accordingly, we took this to be the minimal length of the linear precursor used to form the macrocycle via a copper-catalysed azide alkyne cycloaddition (CuAAC) click reaction. We selected a 1,4-bisalkyl-benzene linker to provide steric shielding of the binding site while allowing for variation in length (compounds 2 and 3). We also considered fluorination of the benzene ring (compounds 4-6), as the unique solubility of perfluoro moieties has been shown to improve ion transport. Compound 6, containing a less polar methyl ester electron withdrawing group, was also synthesised with the aim of improving lipophilic balance. A logP value of 5-6 has previously been shown to be optimum for anion transport, and the calculated values for macrocycles 2-6 ranged from 4.8 to 6.6 (Table ).