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Issue 20, 2012
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Acid-responsive organogel mediated by arene–perfluoroarene and hydrogen bonding interactions

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Abstract

A phenyl and a 2,3,5,6-tetrafluorophenyl ring, each bearing a tris(n-dodecyloxy)benzylamine moiety via an amide bond, were tethered together through an imine linkage to give a non-covalent synthon (imine 1) with a strong capacity of supramolecular self-assembly. Gelation was observed in several organic solutions, within which fibrous aggregate morphologies were visualized by SEM and AFM. Both arene–perfluoroarene stacking and amideamide hydrogen bonding interactions were responsible for such self-assembly behaviours, as evidenced by 1H NMR studies. Hydrolysis of the imine linkage catalyzed by acid strongly weakened the intermolecular interactions, resulting in dissociation of the low molecular weight gelator and giving rise to an acid-mediated gel–sol transition.

Graphical abstract: Acid-responsive organogel mediated by arene–perfluoroarene and hydrogen bonding interactions

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Publication details

The article was received on 01 Dec 2011, accepted on 14 Mar 2012 and first published on 05 Apr 2012


Article type: Paper
DOI: 10.1039/C2SM07281E
Citation: Soft Matter, 2012,8, 5486-5492
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    Acid-responsive organogel mediated by arene–perfluoroarene and hydrogen bonding interactions

    H. Wu, B. Ni, C. Wang, F. Zhai and Y. Ma, Soft Matter, 2012, 8, 5486
    DOI: 10.1039/C2SM07281E

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