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Issue 7, 2000
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A preparative, spectroscopic and equilibrium study of some phenyl-2-thiazoline fluorophores for aluminium(III) detection

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Abstract

As part of a study of fluorophores for selective Al3+ detection and of potential use in the study of intracellular Al3+, the preparative, UV–visible and fluorescence spectroscopic, and Al3+ coordination characteristics of five ligands containing the conjugated phenolic substituted thiazoline chromophore of the natural siderophore, pyochelin, 2-[2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolane-4-carboxylic acid) 1, are reported. The five ligands are 2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid, 2, 2-(4,5-dihydro-1,3-thiazol-2-yl)phenol, 3, 4-bromo-2-(4,5-dihydro-1,3-thiazol-2-yl)phenol, 4, 2-(4,5-dihydro-1,3-thiazol-2-yl)-5-nitrophenol, 5, and 2-(4,5-dihydro-1,3-thiazol-2-yl)-4-nitrophenol, 6. All form stable binary Al3+ complexes in 75% methanol and 25% water in the case of 2, and 73.2% methanol, 24.4% water and 2.4% N,N-dimethylformamide in the case of 36, and exhibit substantial UV–visible absorbance changes on coordination. However, while 2, 3 and 4 fluoresce strongly when coordinated to Al3+, 5 and 6 do not, probably because their fluorescence is quenched through a twisted intramolecular charge transfer process. All five ligands show selectivity in complexing for Al3+ over other metal ions and, in the case of 2, 3 and 4, represent an initial stage in the development of Al3+ specific fluorophores for biological use.

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Publication details

The article was received on 08 Mar 2000, accepted on 12 Apr 2000 and first published on 06 Jun 2000


Article type: Paper
DOI: 10.1039/B001905O
New J. Chem., 2000,24, 541-546

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    A preparative, spectroscopic and equilibrium study of some phenyl-2-thiazoline fluorophores for aluminium(III) detection

    S. G. Lambert, J. M. Taylor, K. L. Wegener, S. L. Woodhouse, S. F. Lincoln and A. David Ward, New J. Chem., 2000, 24, 541
    DOI: 10.1039/B001905O

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