Chirality sensing of choline derivatives is achieved by a self-assembled, racemic triple anion helicate cage which exhibits induced circular dichroism (ICD) upon encapsulation of a chiral guest. The host-guest interactions were illustrated by NMR, crystal structure, CD and DFT calculations. The absolute configurations and ee values were determined by ICD.

In many critical biological processes, host–guest chemistry of protein receptors is regulated by effector molecules to realize cascaded delivery of messenger molecules between different targets. Mimicking these natural processes with artificial receptors remains a challenge. Herein, we report a cascaded guest delivery between two anionocages (anion‐coordination‐driven cages), in a reversible manner, wherein binding of K+ ions by a crown ether functionalized, heteroleptic A2L3 (A=anion, L=ligand) anionocage triggers the release and delivery of a TEA+ (tetraethylammonium) guest to another A2L3 anionocage that is a weaker and less K+‐sensitive receptor. Elimination of the K+ with [2,2,2]‐cryptand enables recapture of the TEA+ by the crown ether functionalized anionocage and thus realizes a reversed guest delivery. Moreover, integrative self‐sorting of anionocages is firstly reported, leading to heteroleptic cages with enhanced guest binding affinities.

Functionalization of oligo-ureas with quaternary ammonium groups leads to water soluble receptors for selective binding of adenosine phosphates in water.