A novel synthetic protocol for aromatic ring substitution in naphthalene 1,4,5,8-tetracarboxylic derivatives

Core-substituted naphthalene diimides (cNDIs) are a class of organic compounds that are rapidly getting interest due to their relevance to a variety of research areas including organic field-effect transistors, organic photovoltaics, solar cells, colorimetric sensors and catalysis. The demand for new efficient synthesis of cNDI requires new methodology for the production of monohalo-substituted anhydrides and 1,4,5,8-naphthalene imides to obtain organic materials of great importance. Here is presented work towards the m-cNDI of a distinct synthesis of cNDI through the selective mono-functionalization of the core by the activation of the palladium-catalyzed C−H bond, promoting carbon-halogen bond formation. The method was optimized by variations in the proportion of the reactants, temperature and reaction time. The products were characterized by H and C NMR, mass spectrophotometer and infrared. And finally, aggregation studies of these compounds were performed with the use of UV-Visible and fluorescence analyzes.