%0 Journal Article %1 mahl2018tetrachlorinated %A Mahl, Magnus %A Shoyama, Dr. Kazutaka %A Rühe, Jessica %A Grande, Dr. Vincenzo %A Würthner, Prof. Frank %D 2018 %J Chemistry - A European Journal %K afm cells myown organic %N 37 %P 9409 –9416 %R DOI:10.1002/chem.201801191 %T Tetrachlorinated Polycyclic Aromatic Dicarboximides: New Electron‐Poor π‐Scaffolds and NIR Emitters by Palladium‐Catalyzed Annulation Reaction %U http://dx.doi.org/10.1002/chem.201801191 %V 24 %X 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 electrondeficient 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 p-extended arrays by metal-mediated coupling reactions.

@article{mahl2018tetrachlorinated, 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 electrondeficient 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 p-extended arrays by metal-mediated coupling reactions. }, added-at = {2018-07-04T09:46:21.000+0200}, author = {Mahl, Magnus and Shoyama, Dr. Kazutaka and Rühe, Jessica and Grande, Dr. Vincenzo and Würthner, Prof. Frank}, biburl = {https://www.bibsonomy.org/bibtex/21d4a9c12cd44a3172702531f0bec8db3/wuerthner_group}, doi = {DOI:10.1002/chem.201801191}, interhash = {2d6204e6d4241627c6457fe0e1f48bca}, intrahash = {1d4a9c12cd44a3172702531f0bec8db3}, journal = {Chemistry - A European Journal}, keywords = {afm cells myown organic}, month = jun, number = 37, pages = {9409 –9416}, timestamp = {2020-06-29T10:58:36.000+0200}, title = {Tetrachlorinated Polycyclic Aromatic Dicarboximides: New Electron‐Poor π‐Scaffolds and NIR Emitters by Palladium‐Catalyzed Annulation Reaction}, url = {http://dx.doi.org/10.1002/chem.201801191}, volume = 24, year = 2018 }