An anthracene-based tripodal chemosensor for anion sensing.
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.
Quinn
Whitney A
WA
Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217, USA. sunshinequinn@yahoo.com
Saeed
Musabbir A
MA
Powell
Douglas R
DR
Hossain
Md Alamgir
MA
D000838:Anions / Q000032:analysis*; D000873:Anthracenes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008024:Ligands; D008958:Models, Molecular; D013050:Spectrometry, Fluorescence
D000838:Anions; D000873:Anthracenes; D008024:Ligands