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A Friedländer route to 5,7-diazapentacenes
A.V. Lunchev, V.C. Hendrata, A. Jaggi, S.A. Morris, , X. Chen, H. Sun, A.C. Grimsdale
Published in Royal Society of Chemistry
Volume: 6
Issue: 14
Pages: 3715 - 3721
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. © This journal is 2018 The Royal Society of Chemistry.
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