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An Anthracene-Based Tripodal Chemosensor for Anion Sensing
Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217, USA
Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA
* Author to whom correspondence should be addressed.
Received: 7 January 2010; in revised form: 31 March 2010 / Accepted: 3 April 2010 / Published: 4 May 2010
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
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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.
Quinn WA, Saeed MA, Powell DR, Hossain MA. An Anthracene-Based Tripodal Chemosensor for Anion Sensing. International Journal of Environmental Research and Public Health. 2010; 7(5):2057-2070.
Quinn, Whitney A.; Saeed, Musabbir A.; Powell, Douglas R.; Hossain, Md. Alamgir. 2010. "An Anthracene-Based Tripodal Chemosensor for Anion Sensing." Int. J. Environ. Res. Public Health 7, no. 5: 2057-2070.