Synthesis, self-assembly, and air-stable radical anions of unconventional 6, 7-bis-nitrated N-annulated perylene diimides. Issue 7 (8th July 2020)

• Record Type: Journal Article
• Authors: Cann, Jonathan; Gelfand, Benjamin Sidney; Welch, Gregory C.
• Is Part Of: Molecular Systems Design and Engineering. Volume 5:Issue 7(2020)
• Page Start: 1181
• Page End: 1185
• Publication Date: 2020-07-08
• Subjects: Chemistry -- Molecular aspects -- Periodicals; Chemical engineering -- Molecular aspects -- Periodicals; Nanotechnology -- Periodicals; 620.5
• DOI: 10.1039/d0me00081g
• Languages: English
• ISSNs: 2058-9689

Abstract

Abstract : Unusual 6, 7-bis-nitrated N -annulated perylene diimides are reported which have stabilized frontier molecular orbitals. The highly stabilized LUMO enables the generation of air-stable radical anions. 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.