Synthesis of 1,6/7-(NO2)2Perylenediimide and 1,6/7-(NH2)2Perylenediimide: Regioisomerically Pure Materials for Organic Electronics

The use of perylenediimide (PDI) building blocks in materials for organic electronic is of considerable interest. The introduction of peripheral groups in their ortho and bay positions radically modify their optoelectronic properties. In this article, we describe an efficient method to afford regioisomerically pure 1,6/7-(NO2)2- and (NH2)2-PDIs employing two key steps: the selective crystallization of 1,6-(NO2)2-perylene-3,4,9,10-tetracarboxy tetrabutylester and the nitration of regiopure 1,7-Br2-PDI with silver nitrite. The optoelectronic properties of the resulting regioisomerically pure dinitro, diamino-PDIs and bisazacoronenediimides (BACDs) are reported and demonstrate the need to separate both regioisomers of such n-type organic semiconductors for their inclusion in advanced optoelectronic devices.