Hydrogen-Bonded Organic Semiconductors with Long Charge Carrier Lifetimes

Abstract

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 two hydrogen-bonded thiophene-capped diketopyrrolopyrrole (DPP) derivatives containing amides with different topology (C- or N-centered) 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 lifetimes compared to other amide-containing semiconductors reported in the literature.