title: Selective recognition of sulfate anions in a 95% ethanol solvent with a simple neutral salicylaldehyde dansyl hydrazine Schiff base tuned by Brønsted-Lowry acid-base reaction.
abstract: A new Schiff base compound, 5-(dimethylamino)-N'-(2-hydroxybenzylidene)naphthalene-1-sulfonohydrazide (R), has been synthesized, characterized, and employed as a selective fluorescence receptor for the recognition of sulfate anions. UV-vis absorption, fluorescence emission, (1)H NMR spectra and DFT calculation studies on the system have been carried out to determine the nature of the interactions between R and anions. The results reveal that the deprotonation of the phenol without the need of a strong base leads to the formation of a hydrogen-bonding complex with a -SO2-NH- group, which is responsible for the spectra changes. The deprotonation process for the selectivity recognition of sulfate can be tuned by the Brønsted-Lowry acid-base reaction in nonaqueous solutions, revealing that suitable phenolic hydroxyl acidity is the key factor for anion recognition selectivity.
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China.
authors.forename: Gao-Ning
authors.initials: GN
authors.lastname: Wei
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China.
authors.forename: Jing-Li
authors.initials: JL
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China.
authors.forename: Cang
authors.initials: C
authors.lastname: Jia
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China.
authors.forename: Wei-Zhen
authors.initials: WZ
authors.lastname: Fan
authors.affiliation: Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, PR China. Electronic address: linlr@xmu.edu.cn.
authors.forename: Li-Rong
authors.initials: LR
authors.lastname: Lin
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D003619:Dansyl Compounds / Q000737:chemistry*; D000431:Ethanol / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry*; D012545:Schiff Bases / Q000138:chemical synthesis / Q000737:chemistry; D013431:Sulfates / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D003619:Dansyl Compounds; D006834:Hydrazines; D012545:Schiff Bases; D013431:Sulfates; C013243:salicylaldehyde; C027913:dansyl hydrazine; D000431:Ethanol
keywords: Brønsted–Lowry acid–base reaction; Excited state proton transfer fluorescence; Recognition; Schiff base; Sulfate anion