Synthesis, self-assembly, and air-stable radical anions of unconventional 6,7-bis-nitrated N-annulated perylene diimides

Abstract

Unusual 6,7-bis-nitrated N-annulated perylene diimides are reported which have stabilized frontier molecular orbitals making them highly electron deficient. Radical anion formation under ambient conditions is readily feasible. A crowded NO₂ substitution pattern significantly alters the perylene core geometry. Varied functionalization at the pyrrolic N-position allows for crystal engineering.