Phenylene bridged cyclic azaacenes: dimers and trimers
The synthesis and characterization of novel macrocyclic, phenylene-bridged azaacenes is reported. These species were obtained either by a conventional benzoin- diamine condensation, as shown for the case of the cyclotrimers, in which the azaacene units are separated by meta-connected phenylene bridg...
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| Main Authors: | , , , , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
31 January 2018
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| In: |
Chemistry - a European journal
Year: 2018, Volume: 24, Issue: 27, Pages: 6968-6974 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201705704 |
| Online Access: | Verlag, Volltext: https://doi.org/10.1002/chem.201705704 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201705704 
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| Author Notes: | Sebastian Hahn, Silke Koser, Manuel Hodecker, Pascal Seete, Frank Rominger, Ognjen Š Miljanić, Andreas Dreuw, Uwe H.F. Bunz |
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| 520 | |a The synthesis and characterization of novel macrocyclic, phenylene-bridged azaacenes is reported. These species were obtained either by a conventional benzoin- diamine condensation, as shown for the case of the cyclotrimers, in which the azaacene units are separated by meta-connected phenylene bridges, or by a Buchwald-Hartwig-type Pd-catalyzed coupling, which employs 1,2,5,6-tetrabromodibenzocyclooctatetraene as the substrate and bis-TIPS-ethynylated diaminobenzene, -naphthalene or -anthracene as the coupling partner to give the double coupling products azaacene-annulated dibenzocyclooctatetraenes in moderate yields. The macrocycles show strong emission and light emitting diodes have been built with brightnesses exceeding 1600 cd m−2. We evaluated the optical and electronic properties and the solid-state structures of the molecules and discuss their properties through comparison with their linear and tetrameric N-heteroacene counterparts. | ||
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