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A Multicontrolled Enamine Configurational Switch Undergoing Dynamic Constitutional Exchange
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. RISE Biosci & Mat, Res Inst Sweden, Forskargatan 18, S-15136 Sodertalje, Sweden.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. Univ Massachusetts Lowell, Dept Chem, 1 Univ Ave, Lowell, MA 01854 USA..
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 Cu-II. 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
Wiley-VCH Verlagsgesellschaft, 2018. Vol. 57, no 21, p. 6256-6260
Keywords [en]
dynamic exchange, enamines, fluorescence, E/Z isomerization, molecular switches
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-230502DOI: 10.1002/anie.201802994ISI: 000432710100049PubMedID: 29601656Scopus ID: 2-s2.0-85046299449OAI: oai:DiVA.org:kth-230502DiVA, id: diva2:1218972
Funder
Swedish Research Council
Note

QC 20180615

Available from: 2018-06-15 Created: 2018-06-15 Last updated: 2018-06-15Bibliographically approved

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Ren, YansongSvensson, Per H.Ramström, Olof

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