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- Title
Tetrachlorinated Polycyclic Aromatic Dicarboximides: New Electron‐Poor π‐Scaffolds and NIR Emitters by Palladium‐Catalyzed Annulation Reaction.
- Authors
Mahl, Magnus; Shoyama, Kazutaka; Rühe, Jessica; Grande, Vincenzo; Würthner, Frank
- Abstract
Abstract: Herein we report a palladium‐catalyzed annulation reaction consisting of a Suzuki–Miyaura cross‐coupling and a C−H arylation cascade for the synthesis of tetrachlorinated polycyclic aromatic dicarboximides (PADIs). This convergent synthetic route afforded a broad series of hitherto unknown electron‐deficient PADIs under optimized reaction conditions by coupling of a dibromo‐tetrachloro‐perylene dicarboximide with different polycyclic aromatic hydrocarbon (PAH) boronic acid pinacol esters in up to 89 % yields. The new PADI compounds show broad absorption in the visible range and some of them emit in the near‐infrared (NIR) region. Cyclic and square wave voltammetric studies revealed that these tetrachlorinated PADIs are more electron‐deficient than a non‐chlorinated reference compound and they possess lower lying frontier orbitals. Thus, the newly synthesized electron‐poor PADIs are potential n‐type semiconductors. Moreover, these chlorinated PADIs are interesting building blocks for the construction of large π‐extended arrays by metal‐mediated coupling reactions.
- Subjects
POLYCYCLIC aromatic compounds; PALLADIUM catalysts; DICARBOXIMIDES; ANNULATION; COUPLING reactions (Chemistry); CARBON-hydrogen bonds
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 37, p9409
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201801191