Azulene‐Based Donor–Acceptor Systems: Synthesis, Optical, and Electrochemical Properties

• Shoji, Taku

• Ito, Shunji

書誌事項

タイトル別名

• Azulene-Based Donor-Acceptor Systems: Synthesis, Optical, and Electrochemical Properties

抄録

First published: 07 Aug 2017

We describe the synthesis and properties of azulene-substituted 1,1,4,4-tetracyanobutadienes (AzTCBDs) and heteroazulenyl TCBDs. TCBD derivatives were prepared in good to excellent yields through reaction of the corresponding 1-ethynylazulenes with tetracyanoethylene (TCNE). In contrast, the reaction between propargyl alcohols and the 1-azulenyl group in TCNE generated 2-aminofuran derivatives, which were transformed into 6-aminofulvenes with a 1-azulenyl substituent upon treatment with several amines. The optical and electrochemical properties of the AzTCBDs were clarified by UV/Vis and voltammetry. The AzTCBD derivatives exhibited electrochromism, showing a multi-step color change under electrochemical redox conditions. The multistage redox properties of AzTCBDs could be useful for the development of novel organic electronic materials.

Article

CHEMISTRY-A EUROPEAN JOURNAL. 95(1):16696-16709 (2017)

収録刊行物

• CHEMISTRY-A EUROPEAN JOURNAL

  CHEMISTRY-A EUROPEAN JOURNAL 23 (66), 16696-16709, 2017-11-27

  WILEY-V C H VERLAG GMBH

キーワード

• azulene
• cycloaddition
• donor-acceptor system
• heteroazulene
• redox chemistry

詳細情報

• CRID: 1050001338927243008
• NII論文ID: 120007100265
• NII書誌ID: AA11076269
• ISSN: 09476539
• ISSN: 15213765
• DOI: 10.1002/chem.201702806
• HANDLE: 10091/00020651
• Web Site: https://soar-ir.repo.nii.ac.jp/records/19890
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.201702806
• Web Site: https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201702806
• 本文言語コード: en
• 資料種別: journal article
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