A 2,6-diformylnaphthalene-1,8:4,5-bis(dicarboximide): synthesis and Knoevenagel condensation with malononitrile.

Ozonolysis of the 2,6-divinyl derivative of a naphthalene diimide (NDI) affords a 2,6-diformyl-NDI, which can be used in Knoevenagel condensation reactions, as demonstrated by the synthesis of a 2,6-bis(2,2-dicyanovinyl)-NDI. UV-vis absorption and electrochemical data are compared to those of the parent NDI.

2,6-Diacylnaphthalene-1,8:4,5-bis(dicarboximides): synthesis, reduction potentials, and core extension.

2,6-Diacyl derivatives of naphthalene-1,8:4,5-bis(dicarboximide)s have been synthesized via Stille coupling reactions of the corresponding 2,6-distannyl derivative with acyl halides. Reaction of these diketones with hydrazine gave phthalazino[6,7,8,1-lmna]pyridazino[5,4,3-gh][3,8]phenanthroline-5,11(4H,10H)-dione fused-ring derivatives. The products were characterized by UV-vis absorption spectroscopy and electrochemistry, modeled using density functional theory calculations, and, in some cases, studied and compared using single-crystal X-ray diffraction.

Hybrid rylene arrays via combination of Stille coupling and C-H transformation as high-performance electron transport materials.

Hybrid rylene arrays have been prepared via a combination of Stille coupling and C-H transformation. The ability to extend the π system along the equatorial axis of rylenes not only leads to broadened light absorption but also increases the electron affinity, which can facilitate electron injection and transport with ambient stability.

Stannyl derivatives of naphthalene diimides and their use in oligomer synthesis.

2-Stannyl and 2,6-distannyl naphthalene diimides (NDIs) can be synthesized through the palladium-catalyzed reaction of the appropriate bromo derivatives with hexabutylditin. The utility of these precursors in palladium catalyzed cross-coupling reactions is demonstrated by the synthesis of bi- and ter-NDI derivatives, UV-vis, cyclic voltammetry, and n-channel organic field-effect transistor data for which are compared to those of the monomeric parent NDI.