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Int. J. Environ. Res. Public Health 2010, 7(5), 2057-2070; doi:10.3390/ijerph7052057
Article

An Anthracene-Based Tripodal Chemosensor for Anion Sensing

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Received: 7 January 2010 / Revised: 31 March 2010 / Accepted: 3 April 2010 / Published: 4 May 2010
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Abstract

An anthracene-based tripodal ligand was synthesized from the condensation of tren with 9-anthraldehyde, and the subsequent reduction with sodium borohydride. The neutral ligand was protonated from the reaction with p-toluenesulfonic acid to give a triply charged chemosensor that was examined for its anion binding ability toward fluoride, chloride, bromide, sulfate and nitrate by the fluorescence spectroscopy in DMSO. The addition of an anion to the ligand resulted in an enhancement in fluorescence intensity at the excitation of 310 nm. Analysis of the spectral changes suggested that the ligand formed a 1:1 complex with each of the anions, showing strong affinity for fluoride and sulfate in DMSO. The unsubstituted tren was reacted with sulfuric acid to form a sulfate complex and the structure was determined by the X-ray crystallography. Analysis of the complex revealed that three sulfates are held between two ligands by multiple hydrogen bonding interactions with protonated amines.
Keywords: Tren; chemosensor; anion complex; fluorescence titrations; anion receptor Tren; chemosensor; anion complex; fluorescence titrations; anion receptor
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Quinn, W.A.; Saeed, M.A.; Powell, D.R.; Hossain, M.A. An Anthracene-Based Tripodal Chemosensor for Anion Sensing. Int. J. Environ. Res. Public Health 2010, 7, 2057-2070.

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