Abstract
Diketopyrrolopyrrole (DPP) is a widely used building block for high-mobility ambipolar semiconductors. Hydrogen bonding of N-unsubstituted DPPs has recently been identified as a tool for controlling their solid state structure and properties of semiconducting films, yet little is known about supramolecular packing of H-bonded DPP derivatives. Here we report a comparative study of three archetypical DPP derivatives, difurylDPP (DFDPP), diphenylDPP (DPDPP), and dithienylDPP (DTDPP), at the interface and in bulk crystals. Using scanning tunneling microscopy (STM) combined with X-ray crystallographic analysis, we demonstrate how the interactions of the (hetero)aromatic substituents interplay with H-bonding, causing dramatic differences in the supramolecular ordering of these structurally similar building blocks. Under all explored conditions, DPDPP exclusively forms H-bonded homoassemblies; DFDPP strongly prefers to co-assemble with alkanoic acids, through a rare lactam···carboxylic acid H-bonded complex, and...
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