Walking a Supramolecular Tightrope: A Self-Assembled Dodecamer from an 8-Aryl-2′-deoxyguanosine Derivative

[Image: see text] Controlling the properties of self-assembled supramolecules via intrinsic parameters (i.e., structural information in the subunits) enables the reliable construction of assemblies of well-defined size and composition. Here we show that an optimum balance between repulsive (e.g., steric) and attractive (e.g., π−π, dipole−dipole) noncovalent interactions between subunits of a lipophilic 8-(3-pyridyl)-2′-deoxyguanosine derivative enables the high fidelity formation of a stable and discrete self-assembled dodecamer. In contrast, the isosteric 8-phenyl-2′-deoxyguanosine derivative assembles into an octamer because it cannot engage in additional dipole−dipole interactions. Adding dodecamers to a supramolecular construction toolbox, already containing octamers and hexadecamers made from other 8-aryl-2′-deoxyguanosine derivatives, should enable the preparation of a wide variety of self-assembled nanostructures where the size and the number of functional elements can be precisely fine-tuned for specific applications.