Supramolecular electronic materials have been widely studied in the last decades due to the exciting properties they have thanks to the interplay of noncovalent interactions. The arrangement of conjugated materials is directed towards well-defined assemblies where not only the structures are improved, but also the properties . Particularly, hydrogen bonds (H-bonds) are noncovalent interactions demonstrated to increase the efficiency of different electronic devices. Nevertheless, their use has been overlooked because the fabrication of electronic devices implies the optimization of multiple parameters, resulting in a large combinatorial space. This turns into a very tedious task when implementing new materials, as for instance, H-bonded molecules. This usually leads to a lack of consensus regarding their incorporation into electronic devices. Still, the proper control of the Hbonded semiconducting structures opens a strategy for the design of alternative organic electronic materials whose properties can be modified through aggregation. Our group and others have studied Hbonded -conjugated molecules containing different H-bonding functionalities, such as semicarbazones, ureas, amides or self-complementary H-bonds to explore the impact of H-bonding in the optoelectronic properties of the assemblies. Amide functionalities are among the bestknown H-bonding forming groups, being the amide topology (N-or C-centered) a subtle, but very important parameter able to change the self-assembly of a given system and hence, the properties. In this work, we show amide-containing thiophene-capped diketopyrrolopyrrole (DPP) derivatives with different amide topology to investigate its influence on the self-assembly, optoelectronic and charge transport properties. We compare two DPP derivatives containing amide groups with N-or Ccentered topology, attached to the lactams through flexible alkyl linkers. To provide solubility, we have added hexyl tails to the thiophene in the extremities of the molecule (Scheme 1). Furthermore, we have also synthesized a DPP molecule having only hexyl alkyl tails in the lactams and the thiophenes as a control. We chose DPP as the -conjugated segment due to its interesting electronic properties and the different positions available for functionalization. We have already explored other families of H-bonded DPP with different H-bonding functionalities to have an overall picture of the role of Hbonds in the optoelectronic properties of DPP supramolecular systems. In this work, we follow the selfassembly processes of the N-and C-centered amide-containing DPP derivatives with different spectroscopy and microscopy techniques, and study the charge transport properties with a contactless technique based on dielectric microwave conductivity. The differences in aggregation and morphology between the two topology amides are discussed, as well as compared to the control molecule not containing H-bonds. Furthermore, we compare the charge transport results of the amide-containing DPPs to the control molecule and to previously reported H-bonded derivatives measured with the same contactless technique. We evaluate the recombination lifetime of the three derivatives and discuss the results according to the molecular design. With our results, we expect to provide new strategies for the design of H-bonded semiconductors with enhanced properties.