Dicyano-Substituted Diazaacenes

• Verfasst von: Müller, Matthias [VerfasserIn]
• Verfasst von: Beglaryan, Stella S. [VerfasserIn]
• Verfasst von: Koser, Silke [VerfasserIn]
• Verfasst von: Hahn, Sebastian [VerfasserIn]
• Verfasst von: Tverskoy, Olena [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Bunz, Uwe H. F. [VerfasserIn]
• Titel: Dicyano-Substituted Diazaacenes
• Verf.angabe: Matthias Müller, Stella S. Beglaryan, Silke Koser, Sebastian Hahn, Olena Tverskoy, Frank Rominger, and Uwe H. F. Bunz
• Umfang: 8 S.
• Fussnoten: Gesehen am 08.08.2018
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Jahr Quelle: 2017
• Band/Heft Quelle: 23(2017), 29, S. 7066-7073
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201700421
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1578362687

Abstract

Herein, we report the synthesis, spectroscopic, and structural properties of novel 2,3-dicyano-substituted azaacenes containing three to six annelated rings as a framework. The targets were prepared by Pd-catalyzed coupling of diamino-bis(tri-isopropylsilylethynyl)benzene, -naphthalene, and -anthracene with either 4,5-dibromophthalonitrile or 6,7-dibromonaphthalene-2,3-dicarbonitrile into the respective N,N′-dihydrodiazaacenes. Oxidation with MnO2 or PbO2 furnishes the dicyano-substituted diazaacenes in reasonable to good yields. An exception is the diazahexacene, where the N,N′-dihydrodiazaacene is difficult to oxidize. Most of the targets could be crystallized and pack in isolated pairs, stacks, and brick-wall motifs. The n-type behavior of these molecules was illustrated in a proof-of-concept organic field-effect transistor, showing mobilities up to 7×10−3 cm2 V−1 s−1.