One of the major goals in systems chemistry is to create molecular assemblies with emergent properties that are characteristic of life. An interesting approach toward this goal is based on mergingd ifferent biological building blocks into synthetic systems with properties arising from the combination of their molecular components. The covalentl inkage of nucleic acids (or their constituents:n ucleotides,n ucleosides and nucleobases) with lipids in the same hybrid molecule leads, for example, to the so-called nucleolipids. Herein, we describen ucleolipids with av ery short sequence of two nucleobases per lipid, which, in combination with hydrophobic effectsp romoted by the lipophilic chain, allow controlo ft he self-assembly of lipidic amphiphiles to be achieved. The presentw ork describes as pectroscopic and microscopy study of the structural features and dynamic selfassembly of dinucleolipids that contain adenine or thymine moieties, either pure or in mixtures. This approach leads to different self-assembled nanostructures, which include spherical, rectangulara nd fibrillara ssemblies, as af unction of the sequence of nucleobases and chiral effects of the nucleolipidsinvolved.W ealso show evidencethat the resulting architectures can encapsulate hydrophobic molecules,r evealing their potential as drug delivery vehicles or as compartmentstoh ost interesting chemistries in their interior.