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ORIGINAL RESEARCH article
Front. Chem.
Sec. Supramolecular Chemistry
Volume 13 - 2025 | doi: 10.3389/fchem.2025.1241625
This article is part of the Research Topic Synthesis of Complex Structures Using Dynamic Covalent Chemistry View all articles
Transfer of structural units through covalent switches -pH-modulated transimination as tool for complex architectures
Provisionally accepted
Adrian-Mihail Stadler 1*
Juan Ramirez 2- 1 UMR7006 Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Strasbourg, France
- 2 Université de Strasbourg, Strasbourg, Alsace, France
Transfer of structural units through covalent switches based on imine exchanges (transiminations), can reversibly be modulated, in the same pot and in a reasonable time, by alternate additions of acid and base. This is illustrated here by means of a dialdehyde Ald, derived from pyridine. With an aromatic amine Am1, it produces a first diimine Im1. Reaction of this diimine Im1 with an aliphatic amine Am2 produces the aliphatic diimine Im2. Addition of acid regenerate the first diimine Im1. Subsequent addition of base produces again the second diimine Im2. The aromatic amines Am1 are aniline-or toluidine-based ones, while the aliphatic ones Am2 are primary alkylamines. Trifluoroacetic acid (TFA) and triethylamine (TEA) are used as pH-triggers. No metal ions are needed to perform the exchanges.
Keywords: Imines, Transimination, Dynamic chemistry, pH, Aldehyde, acid, base, Amine
Received: 16 Jun 2023; Accepted: 03 Mar 2025.
Copyright: © 2025 Stadler and Ramirez. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
* Correspondence:
Adrian-Mihail Stadler, UMR7006 Institut de Science et d'Ingénierie Supramoléculaires (ISIS), Strasbourg, France
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