A persistent radical anion derived from a propeller-shaped perylene bisimide-carbazole pentad.

Stabilizing reactive radical ions promises outstanding performances in photocatalysis, organic optoelectronics and photothermal therapies, but it remains a challenge. In this contribution, we firstly report a persistent radical anion (PBI˙ - -4Cz) derived from a propeller-shaped electron-deficient perylene bisimide-based pentad (PBI-4Cz). Detailed investigations confirm that PBI˙ - -4Cz could intactly exist under inert conditions, and its lifetime is sufficiently prolonged up to more than one week under ambient atmosphere. Such exceptional stability is ascribed to the synergistic effect of the high electron-affinity and structural shielding originating from the compact spatial arrangement of PBI-4Cz. This work contributes to rational design and appropriate chemical construction of stable open-shell species.