High affinity guest have been reported for the macrocyclic host cucurbit[7]uril (CB[7]), enabling widespread applications, but preventing CB[7] materials from being returned to their guest-free state for reuse. Here we present polyhedral boron clusters (carboranes) as strongly-binding, yet easily removable, guests for CB[7]. Aided by a Pd-catalyzed coupling of an azide anion, we prepared boron-functionalized 9<i>-</i>amino and 9-ammonium modified <i>ortho-</i>carboranes that bind to CB[7] with a <i>K<sub>a</sub></i>=10<sup>10</sup> M<sup>-1</sup>. Upon treatment with base, the <i>ortho</i>-carboranes<i> </i>readily undergo deboronation to yield anionic <i>nido</i>-carborane, a poor guest of CB[7], facilitating recovery of guest-free CB[7]. We showcase the utility of the modified <i>ortho</i>-carborane guest by recycling a CB[7]-functionalized resin. With this report, we introduce stimuli-responsive decomplexation as an additional consideration in the design of high affinity host-guest complexes.
Pyrrole- and Naphthobipyrrole-Strapped Calix[4]pyrroles as Azide Anion Receptors
