Synthesis of aminated water-soluble pillar[5]arene

• 1、College of Chemistry, State Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012

Abstract：Pillarenes as novel macrocyclic synthetic host molecules have received intensive and extensive investigation since it was firstly reported in 2008. The synthesis of water-soluble pillarene derivatives is the foundation for expanding their applications in biological systems. In this paper, the intermediate I was synthesized by the reaction of hydroquinone with 1,4-dibromobutane as starting materials. Then, bromo-functionalized pillar[5]arenes (II) were obtained by the reaction of I with paraformaldehyde in the presence of trifluoromethanesulfonic acid. Afterwards, azide-substituted pillar[5]arene (III) was obtained by nucleophilic substitution reaction of II. Finally, aminated pillar[5]arene (IV) which showed a good water-solubility in acidic solution was obtained under catalytic reduction. This synthetic strategy is very straightforward and highly efficient.

Keywords： Aminated pillar[5]arene；water soluble；nucleophilic substitution；pillarene