Issue 5, 2017

Synthesis of largely π-extended naphthalenediimides via C–H activation towards highly soluble and narrow band-gap organic optoelectronic materials

Abstract

Atom-economic coupling reactions based on C–H activation are generally used to synthesize small conjugated systems, but their applications in constructing largely π-conjugated systems have been rarely reported. Herein, we report the preparation of largely π-extended naphthalenediimides (4a–c, with molecular weights of up to 2800) by using efficient palladium-catalyzed C–H/C–H homocouplings, with the yields of up to 94%. The physicochemical properties of 4a–c were studied and they exhibited excellent solubility, thermal stability, quasi-reversible reduction processes, broad and long-wavelength optical absorptions with thin-film optical gaps <1.4 eV and fine-tuned deep LUMO energies (<−4.2 eV), which together with ambient stable electron-transporting behaviors demonstrate their promising applications in optoelectronic devices.

Graphical abstract: Synthesis of largely π-extended naphthalenediimides via C–H activation towards highly soluble and narrow band-gap organic optoelectronic materials

Supplementary files

Article information

Article type
Research Article
Submitted
22 Jan 2017
Accepted
21 Mar 2017
First published
22 Mar 2017

Org. Chem. Front., 2017,4, 823-827

Synthesis of largely π-extended naphthalenediimides via C–H activation towards highly soluble and narrow band-gap organic optoelectronic materials

W. Wu, J. Li, Z. Zhao, X. Yang and X. Gao, Org. Chem. Front., 2017, 4, 823 DOI: 10.1039/C7QO00061H

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