Issue 14, 2018

A Friedländer route to 5,7-diazapentacenes

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

Supplementary files

Article information

Article type
Paper
Submitted
07 Nov 2017
Accepted
03 Jan 2018
First published
03 Jan 2018

J. Mater. Chem. C, 2018,6, 3715-3721

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, 6, 3715 DOI: 10.1039/C7TC05057G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements