Thermally activated delayed fluorescence (TADF) has recently emerged as a promising process with significant potential to advance organic light-emitting diodes (OLEDs) for display applications. The donor-acceptor system is a well-known molecular arrangement exhibiting TADF properties. However, our investigation into the chalcone-based donor-π-acceptor (D-π-A) system (SKG1) reveals that the en-one bridging unit in chalcone plays a crucial role in the reverse intersystem crossing (rISC) process and may be responsible for the existence of two conformational isomers. In stark contrast with the conventional endothermic TADF process, the designed molecule follows a down-converted cold rISC pathway that also from a higher-lying triplet (T) state to the lowest singlet (S) state (in toluene) with remarkably short delayed fluorescence lifetime of 350 ns. Additionally, this rISC process is found to be sensitive to the polarity of the medium. The UV-vis-NIR transient absorption spectroscopy reveals an ultrafast intersystem crossing (ISC) process within <100 ps and the involvement of higher lying triplet state in rISC process. This comprehensive research deepens the understanding of the rISC mechanism and paves the way for developing next-generation OLED materials using D-π-A-based delayed emitters.
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