The water-soluble calixarene bearing p-substituted phosphonic acid groups is accessible in five steps in overall 62% yield, with the hydrogen-bonding prowess of the acidic groups dominating its self-assembly processes. These include the formation of 3.0(3) nin and 20(2) nm nanorafts of the calixarene in water using spinning disc processing, stabilized by acetonitrile, and nanorafts in the gas phase (<= 20 molecules). The 20(2) nin particles transform into 3.0(3) nm particles prior to crystallization into a compact bilayer, whereas crystallization in the presence of large organic molecules gives an expanded bilayer interposed by layers of water molecules.
Clark, T., Makha, M., Sobolev, A., Rohrs, H., Atwood, J. L., & Raston, C. (2008). Engineering Nanorafts of Calixarene Polyphosphonates. Chemistry: A European Journal, 14(13), 3931-3938. https://doi.org/10.1002/chem.200701472