Sugar-functionalized water-soluble pillar[5]arene and its host–guest interaction with fullerene

Abstract

Pillar[5]arenes have attracted much attention as a new member of macrocycles due to their unique symmetrical pillar architecture. Pillar[5]arenes are mostly soluble in organic solvents and slightly soluble in water, thus their application in aqueous media has been limited as a result. It is therefore necessary to design water-soluble pillar[5]arene derivatives. Herein, by the introduction of neutral sugar moieties at both upper and lower rims via click reaction, a neutral water-soluble pillar[5]arene (P5AG) was prepared and characterized well. Furthermore, the host–guest interaction between P5AG and fullerene was investigated in both organic medium and aqueous solution. The host–guest complexation was confirmed by fluorescence, nuclear magnetic resonance, ultraviolet-visible, and Raman spectroscopy.