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Issue 3, 2014
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Competitive binding for triggering a fluorescence response in a hydrazodicarboxamide-based [2]rotaxane

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Abstract

The design and synthesis of an interlocked receptor based on a hydrogen bonded [2]rotaxane containing a hydrazodicarboxamide binding site are reported. An anion recognition process with tetrabutylammonium benzoate triggers the submolecular translational movement of its benzylic amide macrocycle developing a progressive increase of the fluorescence intensity, effectively quenched at the original state. The binding of the anion competes with the hydrogen-bond-connected cyclic component for the bis(urea)-based station pushing it towards a stoppered alkyl chain. Moreover, this interlocked system is able to work as a molecular switch restoring its initial state in two ways, either by an ion exchange reaction or by a high yielding oxidation/reduction sequence.

Graphical abstract: Competitive binding for triggering a fluorescence response in a hydrazodicarboxamide-based [2]rotaxane

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Publication details

The article was received on 04 Sep 2013, accepted on 22 Oct 2013 and first published on 29 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41807C
Citation: Org. Biomol. Chem., 2014,12, 474-478
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    Competitive binding for triggering a fluorescence response in a hydrazodicarboxamide-based [2]rotaxane

    J. Berná, C. Franco-Pujante and M. Alajarín, Org. Biomol. Chem., 2014, 12, 474
    DOI: 10.1039/C3OB41807C

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