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5,7,12,14-Tetrafunctionalized 6,13-Diazapentacenes.

ABSTRACT: The synthesis, property evaluation, and single crystal X-ray structures of four 5,7,12,14-tetrafunctionalized diazapentacenes are presented. The synthesis of these compounds either starts from tetrabromo-N,N-dihydrodiazapentacene or from a diazapentacene tetraketone. Pd-catalyzed coupling or addition of a lithium acetylide gave the precursors that furnish, after further redox reactions, the diazapentacenes as stable crystalline materials. The performance of the tetraphenyl-substituted compound as n-channel semiconductor was evaluated in organic field effect transistors.

SUBMITTER: Xie G 

PROVIDER: S-EPMC7004126 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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5,7,12,14-Tetrafunctionalized 6,13-Diazapentacenes.

Xie Gaozhan G   Hauschild Miriam M   Hoffmann Hendrik H   Ahrens Lukas L   Rominger Frank F   Borkowski Michal M   Marszalek Tomasz T   Freudenberg Jan J   Kivala Milan M   Bunz Uwe H F UHF  

Chemistry (Weinheim an der Bergstrasse, Germany) 20191216 4

The synthesis, property evaluation, and single crystal X-ray structures of four 5,7,12,14-tetrafunctionalized diazapentacenes are presented. The synthesis of these compounds either starts from tetrabromo-N,N-dihydrodiazapentacene or from a diazapentacene tetraketone. Pd-catalyzed coupling or addition of a lithium acetylide gave the precursors that furnish, after further redox reactions, the diazapentacenes as stable crystalline materials. The performance of the tetraphenyl-substituted compound a  ...[more]

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