Catalytic Synthesis of Conjugated Azopolymers from Aromatic Diazides

Conjugated polymers containing main chain azoarene repeat units are synthesized by a dinickel catalyzed N=N coupling reaction of aromatic diazides. The polymerization exhibits broad substrate scope and is compatible with heterocycles commonly featured in high performance organic materials, including...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 143; no. 10; pp. 3975 - 3982
Main Authors Andjaba, John M, Rybak, Christopher J, Wang, Zhiyang, Ling, Jianheng, Mei, Jianguo, Uyeda, Christopher
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.03.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:Conjugated polymers containing main chain azoarene repeat units are synthesized by a dinickel catalyzed N=N coupling reaction of aromatic diazides. The polymerization exhibits broad substrate scope and is compatible with heterocycles commonly featured in high performance organic materials, including carbazole, thiophene, propylenedioxythiophene (ProDOT), diketopyrrolopyrrole (DPP), and isoindigo. Copolymerizations can be carried out using monomer mixtures, and monoazide chain stoppers can be used to install well-defined end groups. Azopolymers possess unique properties owing to the functionality of the azo linkages. For example, protonation at nitrogen results in LUMO lowering and red-shifted absorption bands. Additionally, N=N bonds possess low-lying π* levels, allowing azopolymers to be reversibly reduced under mild conditions.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.1c00447