A Friedländer route to 5,7-Diazapentacenes
A route to compounds with a 5,7-diazapentacene skeleton has been established involving a Friedländer reaction. A diaminodiketone 8 has been made by a novel method and reacted with cyclohexanone to prepare an octa-hydro-5,7-diazapentacene 7a and with tetralone to produce a dibenzotetrahydro-5,7-diaza...
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| Main Authors: | , , , , , , , |
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| 其他作者: | |
| 格式: | Article |
| 語言: | English |
| 出版: |
2018
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| 主題: | |
| 在線閱讀: | https://hdl.handle.net/10356/87092 http://hdl.handle.net/10220/44254 |
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| 機構: | Nanyang Technological University |
| 語言: | English |
| 總結: | A route to compounds with a 5,7-diazapentacene skeleton has been established involving a Friedländer reaction. A diaminodiketone 8 has been made by a novel method and reacted with cyclohexanone to prepare an octa-hydro-5,7-diazapentacene 7a and with tetralone to produce a dibenzotetrahydro-5,7-diazapentacene 7b. Reaction of the diaminodiketone with a diarylethanone followed by oxidation gave a tetrabenzo-5,7-diazapentacene 18b. Compound 7b undergoes solid-state dimerization during single-crystal X-ray analysis. These materials possess lower frontier orbitals than pentacene and show strong absorption and fluorescence which is affected by the presence of acid. In particular 18b shows a remarkable colour change in solution upon addition of acid. These results suggest that suitably functionalised 5,7-diazapentacenes could be promising candidates for optoelectronic applications. |
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