Molecular design of functional hollow three-dimensional molecules bearing internal spaces

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A Nanometer-sized adamantane-based cage with a three-dimensional rigid framework has been designed and synthesized by the Hay acetylene coupling reaction, in which two rigid 1, 3, 5-triethynyladamantane units were connected with phenyldiacetylenic bridge parts. The structure of the molecular cage was determined by NMR, MS and single-crystal X-ray analysis. Decorated molecular cages bearing six functional groups self-assemble into a monolayered spherical vesicle in polar solvents due to hydrophobic interactions or fibrous structures in apolar solvents via hydrogen bonds.