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Two-Step Transformation of Aliphatic Polyketones into pi-Conjugated Polyimines
| 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 | | π‐conjugation | | polyimine | | 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 https://pubs.acs.org/doi/10.1021/acs.joc.9b01119 |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/79062 |
| 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)
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Submitter: 猪熊 泰英
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