Hydrogen-bond-directed giant vesicles of guanosine derivatives in water: formation, structure, and stability

Hydrogen-bond-directed giant supramolecular vesicles (diameter 1.20 +/- 0.30 microm (SD)) of an alkylsilylated deoxyguanosine derivative, 2a, were prepared faciley by mixing a small volume of a 2a/THF solution with water. The formation of 2-D inter-guanine hydrogen-bond networks of 2a within the vesicles was indicated by IR spectra. The vesicle solution was stable enough for more than 30 days, in a wide range of temperatures, and between pH 4 and 10 without showing lysis, fusion, precipitation, or leakage of the encapsulated fluorescent probe. In a typical micrometer-sized vesicle, a sufficiently large internal water phase for encapsulating water-soluble substances was surrounded by a multilamellar membrane 15-20 nm in thickness, which was composed of 6-9 layers of 2-D hydrogen-bond-directed sheet assemblies. AC-mode AFM observation of the vesicle on a silicon substrate further demonstrated the high stability and deformable properties of the vesicle membrane under vacuum or mechanical stress. The formation and properties of the vesicle membrane in water were analyzed from the viewpoint of the 2-D hydrogen-bond-directed sheet assemblies, and the scope of the design principle to use nonpolar soft segments as the shielding units of the hydrogen-bond networks in water is discussed.