The straightforward palladium-catalyzed synthesis protocol toward spiro-fused perylene diimides is developed. The reaction involves two palladium-catalyzed C-H activations and 4-fold C-C bond formation sequence from readily available precursors. This facile and step-economic approach also provides another convenient access to ethylene-bridged dimer (NDP) and further π-extended spiro system (SNTP). In addition, the molecular structure of spirodiperylenetetraimide (SDP) is illustrated to show a three-dimensional (3D) cruciform configuration, and its absorbance is distinctly red-shifted due to the significant spiroconjugation effect. With combined properties of broadened and intensive absorption, aligned LUMO levels, and unique molecular geometry, the spiro-fused PDI system represents a new kind of high-performance semiconducting framework as the electron acceptor in high-efficiency organic solar cells.
Fullerene‐free polymer solar cell devices based on a new acceptor, H‐tri‐PDI that is connected by three perylene diimide (PDI) units via imide position shows a power conversation efficiency of 7.25% with a short circuit current density of 16.5 mA cm−2. Thus H‐tri‐PDI molecules and the method of connecting multiple PDI units via imide position provide a reliable guide for the further development of PDI‐based acceptors.
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