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- W4386994276 abstract "Perylene diimides (PDI) are workhorses in the field of organic electronics, owing to their appealing n-semiconducting properties. Optimization of their performances is widely pursued by bay-atom substitution and diverse imide functionalization. Bulk solids and thin-films of these species crystallize in a variety of stacking configurations, depending on the geometry of the stable conformation of the polyaromatic core. We here demonstrate that 1,7-dibromo-substituted perylene diimides, PDI(H2 Br2 ), possessing a heavily twisted conformation in the gas phase, in solution and in the solids, can be easily flattened in the solid state into centrosymmetric molecules if the polyaromatic cores form π-π stabilized chains. This is achieved by using axial residues with low stereochemical hindrance, as guaranteed by a single CH2 /NH spacer directly linked to the imide function. Structural powder diffraction and DFT calculations on four newly designed species of the PDI(H2 Br2 ) class coherently show that, thanks to the flexibility of the N-X-Ar link (X=CH2 /NH), flat cores are indeed obtained by overcoming the interconversion barrier between twisted atropoisomers, of only 26.5 kJ mol-1 . This strategy may then be useful to induce anomalously flat polyaromatic cores of different kinds (substituted acenes/rylenes) in the solid state, towards suitable crystal packing and orbital interactions for improved electronic performances." @default.
- W4386994276 created "2023-09-25" @default.
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- W4386994276 date "2023-10-06" @default.
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- W4386994276 title "Forcing Twisted 1,7‐Dibromoperylene Diimides to Flatten in the Solid State: What a Difference an Atom Makes" @default.
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- W4386994276 doi "https://doi.org/10.1002/anie.202310445" @default.
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