Synthesis of Amino-Substituted Pyrrole-Fused Perylenebis(dicarboximide) Derivatives by a One-Pot Azidation/Reduction/Cyclization

Amino-substituted pyrrole-fused perylenebis(dicarboximides) have been prepared from tri- or tetrabromoperylene prcursors by using the classical azidation conditions for the substitution of aromatic halogen, that is, NaN3, sodium ascorbate, CuI, and N,N-dimethylethane-1,2-diamine in DMSO/H2O. The pyrrole-fused dyes are highly photochemically and thermally stable, which may be useful for labelling and as building blocks for the synthesis of functional molecular materials.