Synthesis of largely π-extended naphthalenediimides via C–H activation towards highly soluble and narrow band-gap organic optoelectronic materials
Literature Information
Publication Date
2017-03-22
DOI
10.1039/C7QO00061H
Impact Factor
5.281
Authors
Wenting Wu, Zheng Zhao, Xiaodi Yang, Xike Gao
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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N-{3-[Benzyl(methyl)amino]propyl}-9-chloro-5,6,7,8-tetrahydro-2-acridinecarboxamide
CAS Number:
1426944-49-1
Molecular Formula:
C25H28ClN3O
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2-[(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraen-1-yloxy]-1,3-propanediol
CAS Number:
222723-55-9
Molecular Formula:
C23H40O3
![Methyl 3-({2'-[(E)-(hydroxyhydrazono)methyl]-4-biphenylyl}methyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate structure](https://static.chemtradehub.com/structs/149/1499167-72-4-034a.webp "Methyl 3-({2'-[(E)-(hydroxyhydrazono)methyl]-4-biphenylyl}methyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate structure")
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CAS Number:
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Molecular Formula:
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