Supramolecular Assembly of a Succinyl-Calix[4]arene Derivative in Multilamellar Vesicles

Amphiphilic calixarenes are interesting building blocks with high propensity to assemble in well-defined supramolecular architectures. In this work, we report that a succinyl-calix[4]arene derivative (2), exposing four terminal carboxylic acid groups at the calixarene upper rim and four dodecyl chains at the lower rim, forms discrete and stable nanoaggregates in aqueous medium. Field-emission scanning electron microscopy and transmission electron microscopy images showed that the aggregates of 2 possess a spherical shape and a vesicular structure with a multilamellar wall. The vesicular nature was confirmed by encapsulation of a hydrophilic dye rhodamine B. A preliminary study also evidenced that compound 2 increases water solubility of a hydrophobic drug such as curcumin.