Ubiquitous Assembly of Amphiphilic Baskets into Unilamellar Vesicles and Their Recognition Characteristics

An amphiphilic basket of type 1 (339 Å(3)) has been found to assemble into unilamellar vesicles in water. The assembled host encapsulates organophosphonates (OPs) (119-185 A(3)) with a particularly high affinity (Ka ∼ 10(5) M(-1)) toward dimethyl phenylphosphonate (185 Å(3)) whose size and shape resemble that of soman (186 Å(3)). Importantly, the entrapment of OPs prompts a phase transformation of vesicular 1 into nanoparticles or larger vesicles as a function of the shape of the host-guest complex.