Certain amphiphilic modules comprising 3-24 synthons are provided herein. Each synthon is independently selected from aryl, heteroaryl, alicyclic, and heteroalicyclic substituents, wherein each synthon selected is bonded to the next through a linker to form a closed ring that defines a nanopore. One or more lipophilic moieties and one or more hydrophilic moieties are bonded to one or more of the synthons, resulting in the formation of the desired amphiphilic modules. Those modules may be subsequently linked to one another to form two-dimensional close-packed planar arrays, referred to as nanomembranes. Nanomembranes may be useful in filtering certain ionic species from a solution. Selective passage of particular species is determined, in part, by the size of the module's nanopore and the nature of the lipophilic/hydrophobic species attached thereto. Also provided are methods of making and using amphiphilic modules and nanomembranes.