Addition of Heteroatoms to Perylenes

Significance

Beginning with 1-nitroperylene, the authors report the synthesis of three perylene derivatives (1-3) containing an annulated hetero­atom. The conditions used are relatively harsh, which is not uncommon when dealing with perylene derivatives, but allow for the inexpensive and straightforward synthesis of grams of material. In all three cases, the heterocyclic derivatives of perylene show a blue-shifted UV-Vis absorbance and emission when compared to perylene. To demonstrate the synthetic range of their method, the authors elaborate 1-nitroperylene through a Diels-Alder reaction with diethyl maleate followed by the addition of sulfur to form 5.