Understanding and promoting self-assembling processes is a key issue that can give rise to interesting applications in nanotechnology and nanoengineering. A precise control at the molecular level is essential to increase the complexity of evolved DNA supramolecular architectures. In this article, we unveil the minimal level of complexity needed for promoting DNA-templated self-assembly of bifunctional oligonucleotides able to form internucleosidic boronate linkages. Our results highlight the key features required for an efficient control of the assembly/disassembly process, as well as the importance of primers to initiate the oligomerization.