The first example of a heteroditopic receptor capable of cooperative recognition and extraction of ammonium salt (NHX) ion-pairs is described. Consisting of a bidentate 3,5-bis-tellurotriazole chalcogen bond donor binding cleft, the appendage of benzo-15-crown-5 (B15C5) substituents to the tellurium centres facilitates binding of the ammonium cation a co-facial bis-B15C5 sandwich complex, which serves to switch on chalcogen bonding-mediated anion binding potency. Extensive quantitative ion-pair recognition H NMR titration studies in CDCN/CDCl (1 : 1, v/v) solvent media reveal impressive ion-pair binding affinities towards a variety of ammonium halide, nitrate and thiocyanate salts, with the heteroditopic receptor displaying notable ammonium halide salt selectivity. The prodigious solution phase NHX recognition also translates to efficient solid-liquid and liquid-liquid extraction capabilities.
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http://dx.doi.org/10.1039/d4dt01376j | DOI Listing |
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