Semiconductor co-crystal formers enforce face-to-face p-stacking in organic semiconductor building blocks

ORGN 52

Anatoliy Sokolov, tony-sokolov@uiowa.edu and Leonard R. MacGillivray. Department of Chemistry, University of Iowa, 305 Chemistry Building, Iowa City, IA 52242
Organic p-conjugated materials exhibiting electron or hole charge transfer capabilities have received considerable attention in the last decade. While the performance of devices based on such materials is determined primarily by the mobility or the ease of charge transfer, it has been identified that most known organic semiconductors do not possess the extended p-p stacking critical for the achievement of efficient mobility values. In this context, we wish to report a method to reliably control the arrangement of semiconductor building blocks (SBBs) in face-to-face p-stacked assemblies in the crystalline solid state. Specifically, 2,5-bis(4-pyridylethynyl)thiophene and 9,10-bis(4-pyridylethynyl)anthracene are allowed to co-crystallize with a ditopic hydrogen bond donor molecule, namely a resorcinol derivative, acting as a semiconductor co-crystal former (SCCF), as shown in Figure 1. The crystal structure of the pure compounds and related co-crystals will be reported and discussed in the context of engineering solids that exhibit efficient charge-transport properties.