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  • 1.
    Ren, Yansong
    et al.
    Royal Institute of Technology.
    Xie, Sheng
    Royal Institute of Technology;Hunan Univ, Peoples Republic of China.
    Grape, Erik Svensson
    Stockholm University.
    Inge, A. Ken
    Stockholm University.
    Ramström, Olof
    Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. Royal Institute of Technology;Univ Massachusetts Lowell, USA.
    Multistimuli-Responsive Enaminitrile Molecular Switches Displaying H+-Induced Aggregate Emission, Metal Ion-Induced Turn-On Fluorescence, and Organogelation Properties2018In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 42, p. 13640-13643Article in journal (Refereed)
    Abstract [en]

    Multistimuli-responsive enaminitrile-based configurational switches displaying aggregation-induced emission (AIE), fluorescence turn-on effects, and super gelation properties are presented. The E-isomers dominated (>97%) in neutral/basic solution, and the structures underwent precisely controlled switching around the enamine C=C bond upon addition of acid/base. Specific fluorescence output was observed in response to different external input in the solution and solid states. In response to H+, configurational switching resulted in complete formation of the nonemissive Z-H+-isomers in solution, however displaying deep-blue to blue fluorescence (Phi(F) up to 0.41) in the solid state. In response to Cu-II in the solution state, the E-isomers exhibited intense, turn-on, blue-green fluorescence, which could be turned off by addition of competitive coordination. The acid/base-activated switching, together with the induced AIE-effects, further enabled the accomplishment of a responsive superorganogelator. In nonpolar solvents, a blue-fluorescent supramolecular gel was formed upon addition of acid to the E-isomer suspension. The gelation could be reversed by addition of base, and the overall, reversible process could be repeated at least five cycles.

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