Unraveling the unusual effect of fluorination on crystal packing in an organic semiconductor.

Owing to combination of chemical and thermal stability, favorable molecular packing, and efficient electron transport, naphthalene diimide derivatives (NDIs) are promising materials for n-channel organic field effect transistors (OFETs). For tuning the properties of n-conductive organic semiconductors, as well as for improvement of their air stability, fluorination is a frequently used approach. In this study, we demonstrate how very small modification of the molecular structure - fluorine substitution in the p-position of the phenyl rings of N,N'-diphenyl-NDI (Ph-NDI) - dramatically changes the crystal packing but almost does not affect electron transport.