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Issue 27-28, 2005
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Fluorescent alizarin–phenylboronic acid ensembles: design of self-organized molecular sensors for metal ions and anions

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Abstract

Alizarin–phenylboronic acid interactions were used in a new design strategy for self-organized fluorescent sensors of metal ions and anions. First, Alizarin Red S (ARS), which binds effectively to phenylboronic acid (PBA) at neutral conditions in water, proved to be an excellent fluorescent indicator for the selective detection of metal ions; the fluorescent-active ARS–PBA ensemble causes an efficient and selective quenching in the fluorescence by adding metal ions. It was also found that anion-induced phenylboronates can bind effectively to alizarin and greatly enhance the fluorescence in MeOH. The observation makes it possible to design new self-organized anion sensory systems composed of alizarin (as reporter) and phenylboronic acids (PBAs, as receptor), such as PBA or 3-nitrophenylboronic acid (NPBA). By combining spectroscopic studies (UV–vis and fluorescence) and 11B NMR measurements, a ternary complex (Falizarin–PBAs) has been determined. The resulting self-organized sensory system is applicable even to the detection of anions dissolved in water, when liquid [alizarin, PBA, 18-crown-6 in CH2ClCH2Cl]–liquid [KX (X = halogen, OAc, H2PO4) in water at pH 5.5] two-phase extraction is employed.

Graphical abstract: Fluorescent alizarin–phenylboronic acid ensembles: design of self-organized molecular sensors for metal ions and anions

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Article information


Submitted
25 Jan 2005
Accepted
18 Apr 2005
First published
09 May 2005

J. Mater. Chem., 2005,15, 2889-2895
Article type
Paper

Fluorescent alizarinphenylboronic acid ensembles: design of self-organized molecular sensors for metal ions and anions

Y. Kubo, T. Ishida, A. Kobayashi and T. D. James, J. Mater. Chem., 2005, 15, 2889
DOI: 10.1039/B501243K

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