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Competitive Binding for Triggering a Fluorescence Response in a Hydrazodicarboxamide-Based [2]rotaxane

Competitive Binding for Triggering a Fluorescence Response in a Hydrazodicarboxamide-Based [2]rotaxane

José Berná, Carlos Franco-Pujante, Mateo Alajarín

Org Biomol Chem. 2014 Jan 21;12(3):474-8.

PMID: 24270597

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18819891	Tetrabutylammonium benzoate		18819-89-1	Price

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