Synthesis and Redox Properties of 1,3-Dithiole[<i>n</i>]radialenes

• Ueda Masafumi

  Department of Chemistry, School of Science, Kitasato University

• Misaki Yohji

  Department of Applied Chemistry, Graduate School of Engineering, Ehime University Research Unit for Power Generation and Storage Materials, Ehime University Research Unit for Development of Organic Superconductors, Ehime University

Bibliographic Information

Other Title

• 1,3-ジチオール［<i>n</i>］ラジアレン類の合成と酸化還元特性
• 1,3-ジチオール[n]ラジアレン類の合成と酸化還元特性
• 1,3-ジチオール[n]ラジアレンルイ ノ ゴウセイ ト サンカ カンゲン トクセイ

Abstract

[n]Radialenes consisting of an n-membered ring and n exocyclic double bonds are a class of cyclic π-conjugated molecules. They have much attention from the viewpoint of their unique molecular and electronic structures due to the cyclic cross-conjugation systems. Various derivatives substituted at the terminal position of the exomethylene carbons were synthesized so far. The derivatives and analogs of [n]radialene substituted with redox-active 1,3-dithiol-2-ylidenes (DTs) (n=4-6) are of interest as multistep redox systems that n DT sites work. Among them, DT[5]radialene derivatives (9) indicate a unusual redox behavior. However, the detailed studies on the synthesis, structural and electronic properties of 9 are in the process of development for the functional materials. In this paper, we revealed the molecular and electronic structures, significant redox behavior, the reactivity of 9 and its oxidized species. Herein, we introduce the synthesis and redox properties of DT[n]radialenes: hydration reaction of (9)⁴⁺ and the molecular structure of its products (13, 14, 15), the possible mechanism ; the synthesis and properties of analogs bearing aromatic rings (20) and π-extended derivatives (22) of 9; the synthesis and redox properties of TTF-fused donor exhibiting a simultaneous four-or eight-electron transfer (24, 25, 27, 33, 34, 35, 36).

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 77 (12), 1234-1246, 2019-12-01

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• 1,3-dithiol-2-ylidene
• hydrolysis
• π-extended TTF
• radialene
• simultaneous multi-electron transfer

Details

• CRID: 1390846609780274304
• NII Article ID: 130007760854
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.77.1234
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 030115968
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030115968
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/77/12/77_1234/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed