Influence of amide topology on the self-assembly and charge transport of hydrogen-bonded semiconductors

Hydrogen bonds are noncovalent interactions able to improve the electronic properties of self-assembled semiconductors. Nevertheless, it is necessary to control the parameters influencing the formation of hydrogen bonds to achieve hierarchical structures with enhanced properties. In this work, we explore the impact of amide topology (C- or N-centered) in hydrogen-bonded thiophene-capped diketopyrrolopyrrole (DPP) derivatives, and compare them to a control analogue without hydrogen bonds. We demonstrate the differences in the optoelectronic and self-assembly properties of the two amide-containing DPP derivatives, as well as in their charge carrier lifetimes. We prove the superior properties of the hydrogen-bonded derivatives in comparison to the control molecule without hydrogen bonds, and show that our molecular design strategy results in supramolecular structures with particularly long charge carrier lifetime compared to other amide-containing semiconductors reported in literature.