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A Multicontrolled Enamine Configurational Switch Undergoing Dynamic Constitutional Exchange
KTH Royal Institute of Technology, Sweden.
RISE - Research Institutes of Sweden, Bioscience and Materials, Surface, Process and Formulation. KTH Royal Institute of Technology, Sweden.
University of Massachusetts Lowell, USA ; KTH Royal Institute of Technology, Sweden.
2018 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 21, p. 6256-6260Article in journal (Refereed) Published
Abstract [en]

A multiresponsive enamine-based molecular switch is presented, in which forward/backward configurational rotation around the C=C bond could be precisely controlled by the addition of an acid/base or metal ions. Fluorescence turn-on/off effects and large Stokes shifts were observed while regulating the switching process with CuII. The enamine functionality furthermore enabled double dynamic regimes, in which configurational switching could operate in conjunction with constitutional enamine exchange of the rotor part. This behavior was used to construct a prototypical dynamic covalent switch system through enamine exchange with primary amines. The dynamic exchange process could be readily turned on/off by regulating the switch status with pH.

Place, publisher, year, edition, pages
2018. Vol. 57, no 21, p. 6256-6260
Keywords [en]
dynamic exchange, E/Z isomerization, enamines, fluorescence, molecular switches, Metal ions, Metals, Dynamic regimes, Exchange process, Multi-responsive, Primary amines, Switch systems, Switching process, Amines
National Category
Natural Sciences
Identifiers
URN: urn:nbn:se:ri:diva-34446DOI: 10.1002/anie.201802994Scopus ID: 2-s2.0-85046299449OAI: oai:DiVA.org:ri-34446DiVA, id: diva2:1237296
Note

The study was in part supported by the Swedish Research Council. Y.R. thanks the China Scholarship Council for a special scholarship award.

Available from: 2018-08-08 Created: 2018-08-08 Last updated: 2019-01-02Bibliographically approved

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