Azido-perylenediimide: a versatile building block for CuAAC reactions and an alternative precursor for N-annulation

Abstract

Azido-perylenediimide (N₃-PDI) was isolated as a stable solid, which readily converts into N-annulated PDI in solution only when exposed to visible light. N₃-PDI was also engaged in CuAAC reactions with alkynes to provide multi-PDI chromophore architectures in excellent yields. This new, easily accessible and highly reactive building block completes the PDI chemistry toolbox for the design of n-type semiconductors and new dyes.