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

Content Provider	Semantic Scholar
Author	Wu, Wenting Li, Jing Zhao, Zheng Yang, Xiaodi Gao, Xike
Copyright Year	2017
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.
Starting Page	823
Ending Page	827
Page Count	5
File Format	PDF HTM / HTML
DOI	10.1039/C7QO00061H
Volume Number	4
Alternate Webpage(s)	http://www.rsc.org/suppdata/c7/qo/c7qo00061h/c7qo00061h1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/C7QO00061H
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article