A Twist in Biphthalimide-Based Chromophores Enables Thermally Activated Delayed Fluorescence

Thermally activated delayed fluorescence (TADF) emitters, which convert nonemissive triplets into emissive singlets, have garnered tremendous impetus as next-generation organic electroluminescent materials. Employing donor-acceptor (D-A) designs to produce intramolecular charge transfer (ICT) states is considered an attractive strategy to effectively reduce the singlet-triplet (�EST) gap, thereby enhancing reverse intersystem crossing (rISC) in TADF emitters. Herein, we report two ICT chromophores (BP-1TPA and BP-2TPA) utilizing a rational design strategy based on a twisted biphthalimide acceptor core integrated with varying triphenylamine donors. We accomplish efficient TADF emission with a high photoluminescence quantum yield (PLQY) of �80 at ambient conditions from poly(methyl methacrylate)-doped films of these chromophores. Twisting the acceptor core ensures the separation of natural transition orbitals, leading to small �EST and generates an intermediate triplet excited state to facilitate rISC. The present study, therefore, sheds light on how delayed fluorescence can be realized from a simple twisted phthalimide core by rational molecular engineering and enables new insights toward exploring the aromatic imide class of molecules as potential organic light-emitting materials. © 2024 American Chemical Society.