Dicyano-Substituted Diazaacenes
Herein, we report the synthesis, spectroscopic, and structural properties of novel 2,3-dicyano-substituted azaacenes containing three to six annelated rings as a framework. The targets were prepared by Pd-catalyzed coupling of diamino-bis(tri-isopropylsilylethynyl)benzene, -naphthalene, and -anthrac...
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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
14 March 2017
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| In: |
Chemistry - a European journal
Year: 2017, Volume: 23, Issue: 29, Pages: 7066-7073 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201700421 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201700421 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201700421 
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| Author Notes: | Matthias Müller, Stella S. Beglaryan, Silke Koser, Sebastian Hahn, Olena Tverskoy, Frank Rominger, and Uwe H. F. Bunz |
| Summary: | Herein, we report the synthesis, spectroscopic, and structural properties of novel 2,3-dicyano-substituted azaacenes containing three to six annelated rings as a framework. The targets were prepared by Pd-catalyzed coupling of diamino-bis(tri-isopropylsilylethynyl)benzene, -naphthalene, and -anthracene with either 4,5-dibromophthalonitrile or 6,7-dibromonaphthalene-2,3-dicarbonitrile into the respective N,N′-dihydrodiazaacenes. Oxidation with MnO2 or PbO2 furnishes the dicyano-substituted diazaacenes in reasonable to good yields. An exception is the diazahexacene, where the N,N′-dihydrodiazaacene is difficult to oxidize. Most of the targets could be crystallized and pack in isolated pairs, stacks, and brick-wall motifs. The n-type behavior of these molecules was illustrated in a proof-of-concept organic field-effect transistor, showing mobilities up to 7×10−3 cm2 V−1 s−1. |
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| Item Description: | Gesehen am 08.08.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201700421 |