Guanosine‐based Hydrogen‐bonded Scaffolds: Controlling the Assembly of Oligothiophenes

The controlled and preprogrammed self-assembly of p-conjugated rodand disc-like oligomers into ordered and anisotropic architectures is an important goal in view of the tailoring of their physico-chemical properties and, ultimately, for their application in molecularand nanoelectronics. Among weak interactions, p-stacking has been the first to be employed to drive the self-assembly of conjugated (macro)molecular systems into well-defined nanoscale assemblies that feature a high degree of order at the supramolecular level. Later, other types of weak yet directional non-covalent interactions, in particular H-bonds, have been used to form both monoand multicomponent p-conjugated architectures, and their application in the fabrication of optoelectronic device prototypes such as photovoltaic diodes and ambipolar transistors has been attempted. Lipophilic guanosines are very versatile building blocks: depending on the experimental conditions they can undergo different self-assembly pathways, leading to the formation of either H-bonded ribbons or quartet-based columnar structures (Fig. 1). Given the possibility to functionalize the guanosines in the side-chains they appear as ideal building blocks for the fabrication of complex architectures with a controlled high rigidity, thus paving the way towards their future use for