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

Haruki Sanematsu, Yoshitaka Matsushita, Masayuki Takeuchi, Atsuro Takai

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)934-938
Number of pages5
JournalChemistry - A European Journal
Volume27
Issue number3
DOIs
Publication statusPublished - 2021 Jan 13
Externally publishedYes

Keywords

  • Michael addition
  • aromatic diimide
  • click chemistry
  • electron-deficient π-system
  • hydroamination

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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