Monofunctionalized pillar[5]arenes: synthesis and supramolecular structure

The first synthesis of a monohydroxy pillar[5] arene has been carried out, by controlling the de-O-methylation of per-methylated pillar[5] arene. Using monohydroxy pillar[5] arene as an intermediate, mono-guest-functionalized pillar[5] arene was prepared. It formed a self-inclusion complex in CDCl3 whereas in acetone-d(6) dethreading of the guest moiety took place.