We have synthesized and characterized two different topology amide-containing DPP derivatives and a control analogue without H-bonding units. The differences in self-assembly properties between the C-and N-centered amide topologies have been demonstrated, as well as their distinct charge carrier recombination lifetimes. Interestingly, the comparison to the control molecule has shown one order of magnitude superior photoconductivity for the H-bonded molecules as well as one order of magnitude slower recombination lifetimes, stressing the beneficial role of H-bonding in the charge transport properties of supramolecular systems. Furthermore, we have found out that with this particular molecular design, placing the H-bonding units between two alkyl spacers, longer recombination times are obtained comparing to previously reported supramolecular systems measured by the same technique. These results are very relevant for the future design and implementation of H-bonded semiconductors into electronic devices with long charge carrier lifetimes.