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Planar Chiral Carbazole-Naphthalene Bisimide Hetero-Cyclophane for Circularly Polarized Delayed Fluorescence
Sanchari Debnath1, Swadhin Garain2, Yvonne Wagenhäuser2
1Center For Nanosystems Chemistry (CNC), Universität Würzburg, Würzburg, Germany.
None:
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 |glum| values of ∼ 2.5 - 3.3 × 10-3.
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