Synthesis, characterization, and self-assembly of nitrogen-containing heterocoronenetetracarboxylic acid diimide analogues: photocyclization of N-heterocycle-substituted perylene bisimides.

Novel dibenzocoronenetetracarboxylic acid diimide analogues and naphthoperylenetetracarboxylic acid diimide analogues containing imidazole, 1,2,4-triazole, and pyrazole rings embedded as functional constituents within the parent hydrocarbon backbone have been synthesized. The pi-rich and pi-poor heterocycles have different influences on the physical properties of the parent benzocoronenetetracarboxylic acid diimide and naphthoperylenetetracarboxylic acid diimide systems. The pi-rich 3 was able to self-assemble into one-dimensional nanostructures through strong pi-pi stacking, whereas the pi-poor 8 lacked the one-dimensional self-assembly capability, thus offering the potential to control the self-assembly capability of the pi-conjugated perylene core by decoration with N-heterocycles.