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Updated: Jan 5, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
5,7,12,14-Tetrafunctionalized 6,13-Diazapentacenes
Gaozhan Xie1, Miriam Hauschild1, Hendrik Hoffmann1
1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
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.
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