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Two-Step Transformation of Aliphatic Polyketones into pi-Conjugated Polyimines

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Title: Two-Step Transformation of Aliphatic Polyketones into pi-Conjugated Polyimines
Authors: Manabe, Yumehiro Browse this author
Uesaka, Mitsuharu Browse this author
Yoneda, Tomoki Browse this author
Inokuma, Yasuhide Browse this author →KAKEN DB
Keywords: polyketone
organic chromophore
Issue Date: 16-Aug-2019
Publisher: American Chemical Society
Journal Title: Journal of organic chemistry
Volume: 84
Issue: 16
Start Page: 9957
End Page: 9964
Publisher DOI: 10.1021/acs.joc.9b01119
Abstract: The chemo- and stereo-selective two-step transformation of aliphatic polyketones composed of 3,3-dimethylpentane-2,4-dione units was achieved to generate pi-conjugated polyimines. Upon treatment with hydrazine, discrete oligoketones with 4-8 carbonyl groups afforded ethylene-bridged oligoisopyrazoles in 80-89% yields. These oligoisopyrazoles underwent stereoselective oxidation at the ethylene bridge to give fully pi-conjugated oligo(isopyrazole-3,5-diyl-trans-vinylene)s in 73-87% yields. Oxidation of the oligoimines drastically changed their absorption and metal-coordination behaviors. Finally, this two-step transformation was applied to polydisperse polymers. Imine formation proceeded almost quantitatively, even for longer polyketones, including docosamer. Subsequent oxidation of the polyimines furnished a virtually insoluble material that showed broad and red-shifted solid-state absorption over the whole visible region resulting from extended pi-conjugation.
Rights: This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of organic chemistry, copyright c American Chemical Society after peer review. To access the final edited and published work see
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 猪熊 泰英

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