Regiochemically Pure 1,6-Ditriflato-Perylene Diimide: Preparation and Transformation

Preparation of regioisomerically pure 1,6-disubstituted perylene diimide (PDI) is not a trivial task owing to the lack of facile synthetic and separation methodologies for the precursors. Herein, we present a simple synthesis for 1,6-ditriflato-PDI (1,6-diOTf-PDI) using 1,6,9,10-tetrabromo-perylene monoimide 1 as the starting material. The selective methoxylation of 1 at the 1,6-position is the key step. Based on a four-step sequence of selective methoxylation, domino carbonylative amidation, demethylation, and triflation, 1,6-diOTf-PDI can be obtained in a satisfactory yield. Moreover, as a building block, 1,6diOTf-PDIa can readily undergo Suzuki and Sonogashira cross coupling reactions.

Automated summary

Here, we present a simple synthesis method for the preparation of 1,6-disubstituted perylene diimide using a tetrabromo-perylene monoimide as the starting material. Through a selective methoxylation, domino carbonylative amidation, demethylation, and triflation sequence, the desired product can be obtained in satisfactory yield. Moreover, the obtained compound can be further used in Suzuki and Sonogashira cross coupling reactions.