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

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