Complementary amide-based donor-acceptor with unique nano-scale aggregation, fluorescence, and bandgap lowering properties: a WORM memory device.

Organic fluorescent semiconducting nanomaterials have gained widespread research interest owing to their potential applications in the arena of high-tech devices. We have designed two pyrazaacene-based compounds, their stacked system, the role of gluing interactions to fabricate nanomaterials, and determined the prospective bandgaps utilizing the DFT calculation. The two pyrazaacene derivatives containing complementary amide linkages (-CONH and -NHCO) were efficiently synthesized. The synthesized compounds are highly soluble in common organic solvents as well as highly fluorescent and photostable. The heterocycles and their mixture displayed efficient solvent dependent fluorescence in the visible region of the solar spectrum. Notably, the compounds were associated through complementary NH•••O=C type hydrogen bonding, π-π stacking, and hydrophobic interactions and thereby afforded nanomaterials with a low bandgap. Fascinatingly, the fabricated stacked nanomaterial system exhibited resistive switching behavior leading to the fabrication of an efficient write once read many times (WORM) memory device of crossbar structure.