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 () using 1,6,9,10-tetrabromo-perylene monoimide as the starting material. The selective methoxylation of at the 1,6-position is the key step. Based on a four-step sequence of selective methoxylation, domino carbonylative amidation, demethylation, and triflation, can be obtained in a satisfactory yield. Moreover, as a building block, can readily undergo Suzuki and Sonogashira cross-coupling reactions.