Amino-Functionalization of Vinyl-Substituted Aromatic Diimides by Quantitative and Catalyst-Free Hydroamination**

Haruki Sanematsu, Yoshitaka Matsushita, Masayuki Takeuchi, Atsuro Takai

研究成果: Article査読

1 被引用数 (Scopus)

抄録

Development of facile and versatile synthetic tools for decorating π-conjugated molecules has attracted considerable interest because of their potential application in creating novel functional π-systems. Reported herein are quantitative catalyst-free hydroamination reactions of a series of aromatic diimide compounds having vinyl groups at the π-core, which have been confirmed by NMR, UV-vis absorption spectroscopy, mass analysis, and single-crystal X-ray structural analysis. Kinetic studies revealed that the hydroamination reaction of a vinyl-substituted naphthalenediimide with an aliphatic amine proceeded rapidly under benign conditions. Similarly, the two vinyl groups attached to aromatic diimides reacted with amines simultaneously, resulting in the formation of amine bisadducts and macromolecules. An amino group appended perylenediimide through an ethylene spacer at the π-core exhibited distinct fluorescence switching in response to acid and base.

本文言語English
ページ(範囲)934-938
ページ数5
ジャーナルChemistry - A European Journal
27
3
DOI
出版ステータスPublished - 2021 1 13
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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