Hydrogen bonds can efficiently guide the self-assembly of organic materials, enabling to tune the properties of the aggregation processes. In the case of p-conjugated materials, several parameters such as temperature, concentration and solvent can be used to modify the aggregation state while tuning the optoelectronic properties. Chirality can be included within the impacting parameters due to the differences in molecular packing. Here, chiral and achiral thiophene-capped diketopyrrolopyrrole derivatives were designed and synthesized containing amide bonds, with the aim to study the interplay between chiral assemblies and their stabilization throughh ydrogen-bonding. Differences in aggregation properties were observed with spectroscopy and microscopy,a nd ac ontactless microwave-based technique was used to study their intrinsic chargec arrierm obility.T he positive role of hydrogen-bonding has been highlighted and the differences between chiral and achiral compoundsh ave been elucidated.

The impact of H-bonding on the optoelectronic properties and device morphology of diketopyrrolopyrrole derivatives is reviewed.