Amino-Functionalization of Vinyl-Substituted Aromatic Diimides by Quantitative and Catalyst-Free Hydroamination

Development of facile and versatile synthetic tools for decorating π-conjugated molecules has attracted considerable interest because of their potential application in creating novel π-electron materials. Reported herein are quantitative catalyst-free hydroamination reactions of a series of aromatic diimide compounds having vinyl groups at the π-core, which have been confirmed by NMR, UV–vis absorption spectroscopy, mass analysis, and single crystal X-ray structural analysis. Kinetic studies revealed that the hydroamination reaction of a vinyl-substituted naphthalenediimide with an aliphatic amine proceeded rapidly under benign conditions. Similary, the two vinyl groups attached to aromatic diimides reacted with amines simultaneously, resulting in the formation of amine bisadducts and macromolecules.