Synthesis of Triptycene-Substituted Azapentacene and Azahexacene Derivatives.
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 absof 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.
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Philipp
P
Biegger
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Olena
O
Tverskoy
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Frank
F
Rominger
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany. uwe.bunz@oci.uni-heidelberg.de.|Centre for Advanced Materials, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 225, 69120, Heidelberg, Germany. uwe.bunz@oci.uni-heidelberg.de.
Uwe H F
UH
Bunz
azaacenes; condensation reactions; cyclobutadiene; homogeneous catalysis; triptycene