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A Friedländer route to 5,7-diazapentacenes

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Abstract

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.

Graphical abstract: A Friedländer route to 5,7-diazapentacenes

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Publication details

The article was received on 07 Nov 2017, accepted on 03 Jan 2018 and first published on 03 Jan 2018


Article type: Paper
DOI: 10.1039/C7TC05057G
Citation: J. Mater. Chem. C, 2018, Advance Article
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    A Friedländer route to 5,7-diazapentacenes

    A. V. Lunchev, V. C. Hendrata, A. Jaggi, S. A. Morris, R. Ganguly, X. Chen, H. Sun and A. C. Grimsdale, J. Mater. Chem. C, 2018, Advance Article , DOI: 10.1039/C7TC05057G

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