Synthesis of Triptycene‐Substituted Azapentacene and Azahexacene Derivatives |
| |
Authors: | Dr. Philipp Biegger Olena Tverskoy Dr. Frank Rominger Prof. Dr. Uwe H. F. Bunz |
| |
Affiliation: | 1. Organisch-Chemisches Institut, Ruprecht-Karls-Universit?t Heidelberg, Heidelberg, Germany;2. Centre for Advanced Materials, Ruprecht-Karls-Universit?t Heidelberg, Heidelberg, Germany |
| |
Abstract: | We describe the synthesis and characterization of novel iptycene‐substituted azaacenes by using either a classic condensation route (diamine plus ortho‐quinone) and/or a Pd‐catalyzed coupling of an aromatic diamine with an aromatic dihalide. The attachment of an iptycene unit leads to a significant blueshift (15 nm) in the UV/Vis spectra of these azaacenes. The iptycene unit stabilizes a hexaazahexacene with a λmax abs of 833 nm. By employing 5,6‐diamino(benzothiadiazole) as a synthon for tetraaminobenzene, we could prepare the symmetrical bis‐triptycene‐substituted tetraazapentacene in high yields. |
| |
Keywords: | azaacenes condensation reactions cyclobutadiene homogeneous catalysis triptycene |
|
|