Planar Chiral Carbazole-Naphthalene Bisimide Hetero-Cyclophane for Circularly Polarized Delayed Fluorescence

Additional Data to report: https://doi.org/10.1002/anie.2300390 Chiral organic chromophores with circularly polarized thermally activated delayed fluorescence (CP–TADF) provide great prospects as circularly polarized luminescence (CPL) emitters owing to the involvement of long-lived triplet excitons. Here, we construct a tailored planar chiral hetero-cyclophane ( NBICz-Cy ) composed of 1,2:5,6–naphthalene bisimide (1,2:5,6–NBI) and carbazole (Cz) units, which functions as an efficient solution-state CP–TADF emitter. Comprehensive photophysical studies reveal pronounced delayed fluorescence in the orange-red region, with a quantum yield (QY) of 19% in deaerated solution and 12% in an aerated solution-processable matrix. Single-crystal XRD analysis unravels a through-space charge-transfer (CT) interaction between the NBI and Cz moieties, being responsible for delayed fluorescence. The inherent prochirality of the 1,2:5,6–NBI moiety imparts planar chirality in the cyclophane framework, resulting in CP–TADF in both solution and solid state with a |glum | value of ∼ 2.5 –3.3 ×10−3.