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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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Bibliographic Details
Main Authors: Hahn, Sebastian (Author) , Koser, Silke (Author) , Hodecker, Manuel (Author) , Seete, Pascal (Author) , Rominger, Frank (Author) , Dreuw, Andreas (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: 31 January 2018
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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Summary: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.
Item Description:Gesehen am 20.08.2019
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201705704

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