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Title: A Friedländer route to 5,7-Diazapentacenes
Authors: Lunchev, Andrey V.
Hendrarta, Vincent Chandra
Jaggi, Aparna
Morris, Samuel Alexander
Ganguly, Rakesh
Chen, Xiaoxuan
Sun, Handong
Grimsdale, Andrew Clive
Keywords: Heteroacenes
Organic Semiconductors
Issue Date: 2018
Source: Lunchev, A. V., Hendrarta, V. C., Jaggi, A., Morris, S. A., Ganguly, R., Chen, X., et al. (2018). A Friedländer route to 5,7-Diazapentacenes. Journal of Materials Chemistry C, in press.
Series/Report no.: Journal of Materials Chemistry C
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.
ISSN: 2050-7526
DOI: 10.1039/C7TC05057G
Rights: © 2018 Royal Society of Chemistry. This is the author created version of a work that has been peer reviewed and accepted for publication by Journal of Materials Chemistry C, Royal Society of Chemistry. It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document. The published version is available at: [].
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:MSE Journal Articles
SPMS Journal Articles

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