Synthesis of cyclodextrin‐based radial polycatenane cyclized by amide bond and subsequent fabrication of water‐soluble derivatives

Abstract

In recent years, functional materials using cyclodextrin (CD)-based polyrotaxanes have attracted considerable attention, and derivatization reactions are often performed to develop them because of the insolubility of the parent polyrotaxane in water. Recently, we prepared CD-based radial polycatenanes in one-pot through polypseudorotaxane formation between β-CD and thiolated pluronic and subsequent cyclization via disulfide bonds. However, no reports are available on syntheses of CD polycatenane derivatives. The disulfide bonds are not stable enough to synthesize CD polycatenane derivatives; therefore, we herein prepared a chemically stable β-CD polycatenane via amide bond through cyclization of β-CD/aminated pluronic polypseudorotaxane with terephthaloyl chloride. This allowed the derivatization of the polycatenane owing to its stable chemical structure, and resulted in the syntheses of three different water soluble polycatenane derivatives: aminated, succinylated, and hydroxypropylated polycatenanes. These findings may provide useful information for the fabrication of polycatenane-based materials such as slide-ring materials, drug carriers, and biomaterials.