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Amino‐Functionalization of Vinyl‐Substituted Aromatic Diimides by Quantitative and Catalyst‐Free Hydroamination **
Author(s) -
Sanematsu Haruki,
Matsushita Yoshitaka,
Takeuchi Masayuki,
Takai Atsuro
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003628
Subject(s) - hydroamination , chemistry , amine gas treating , catalysis , macromolecule , polymer chemistry , surface modification , molecule , functional group , organic chemistry , combinatorial chemistry , polymer , biochemistry
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.