2,3:6,7‒Naphthalene bis(dicarboximide) Cyclophane: A Photo‒functional Host for Ambient Delayed Fluorescence in Solution

Additional data to report https://doi.org/10.1002/anie.202411102:

Harvesting triplet excitons of heavy atom-free purely organic chromophores under aerated conditions is challenging due to the quenching of long-lived triplet states by molecular oxygen and vibrational dissipation. Herein, we show a supramolecular approach of triplet harvesting via mitigating quenching pathways of a triplet harvester. Specifically, we used a host–guest system based on 2,3:6,7‒naphthalene bis(dicarboximide)-derived cyclophane (NBICy) and carbazole derivative (EtCz). Complexation studies and single-crystal X-ray analysis showed the formation of a rigid host–guest complex (K = ~104 M-1 in CCl4), resulting in triplet-exciton stabilization under aerated conditions via mitigating vibrational interference and oxygen quenching. Photophysical studies elucidate the delayed fluorescence emission from the charge-transfer state (1CT) with a quantum yield (QY) of 6-8% under ambient conditions which increased up to 36 % in an inert atmosphere.