Step-Growth Cyclo-Oligomerization for the Preparation of Functionalized Pillar[6]arenes with Alternating Methylene Bridge Substitutions.

Methylene-bridge-substituted pillar[6]arenes (PA[6]) are synthesized by step-growth cyclo-oligomerization. Dimers, trimers, tetramers, and hexamers with substituted methylene bridges are synthesized. Hexamers are converted to PA[6] derivatives with alternating methylene bridge substitutions by ring-closing reactions. PA[6] derivatives are further modified with pyrene groups or carboxylate groups by Suzuki-Miyaura coupling reactions. The modifications render PA[6] fluorescent or water-soluble. A host-guest chemistry study confirms that the water-soluble PA[6] derivative is a high-affinity host toward suitable guests in water.