New Synthetic Route to Water‐Soluble Prism[5]arene Hosts and Their Molecular Recognition Properties**

for a select guest. The complexation events are driven by the non-classical hydrophobic effect, CH⋅⋅⋅π interactions, and electrostatic interactions. Host H1 displays somewhat higher affinity toward a common guest than pillar[6]arene bearing carboxylic acid functional groups but is significantly less potent than pillar[6]arene bearing sulfate groups. H1 and H3 should be considered alongside other high affinity hosts for a variety of chemical and biological applications.