Anion Binding of a Protonated Tripodal Tris(ferrocenylurea) Receptor

Li, Minrui; Wu, Biao; Cui, Fengjuan; Hao, Yajiang; Huang, Xiaojuan; Xiao, Yang

doi:10.1002/zaac.201100214

Cited by 7 publications

(10 citation statements)

References 66 publications

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“…Previously reported urea-based receptors linked with ethylene chains showed stronger binding for SO 4 2− than HSO 4 − , in DMSO- d 6 . 20h,23a Thus, the expansion of the tripodal cavity with propylene chains leads to the change of the selectivity patterns for HSO 4 − and SO 4 2− , showing greater selectivity for HSO 4 − . As compared to ethylene-chain analogues, 20h,23a, 23b the propylene chains in L1 and L2 might result in the higher basicity of the central nitrogen, which could be due to the weaker inductive effect 29 of urea/thiourea groups through the longer propylene chains.…”

Section: Resultsmentioning

confidence: 99%

“…20,21 For example, a m -cyanophenyl-based tripodal urea reported by Custelcean et al was shown to form a silver-based MOF that encapsulated sulfate by a total of twelve hydrogen bonds. 20a Wu et al reported a 3-pyridyl-based tripodal urea that also showed strong affinity for sulfate. 20b Ghosh et al reported a pentafluorophenyl-based tripodal urea for the selective binding of phosphate.…”

Section: Introductionmentioning

confidence: 99%

“…20a Wu et al reported a 3-pyridyl-based tripodal urea that also showed strong affinity for sulfate. 20b Ghosh et al reported a pentafluorophenyl-based tripodal urea for the selective binding of phosphate. 20c A m -nitrophenyl substituted tripodal urea synthesized by Das et al was found to form capsular complexes with carbonate and sulfate.…”

Section: Introductionmentioning

confidence: 99%

“…20b Ghosh et al reported a pentafluorophenyl-based tripodal urea for the selective binding of phosphate. 20c A m -nitrophenyl substituted tripodal urea synthesized by Das et al was found to form capsular complexes with carbonate and sulfate. 20h The progression from urea to thiourea leads to an enhanced acidity of a NH group in the later, thereby a thiourea could have a stronger affinity for an anion than its urea analogue.…”

Section: Introductionmentioning

confidence: 99%

“…20c A m -nitrophenyl substituted tripodal urea synthesized by Das et al was found to form capsular complexes with carbonate and sulfate. 20h The progression from urea to thiourea leads to an enhanced acidity of a NH group in the later, thereby a thiourea could have a stronger affinity for an anion than its urea analogue. 22 Gale et al reported a phenyl-based thiourea tripodal receptor that formed a carbonate complex from a mixture of the host with [Et 4 N][HCO 3 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and anion binding studies of tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors: proton transfer-induced selectivity for hydrogen sulfate over sulfate

et al. 2015

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Tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors, tris([(4-cyanophenyl)amino]propyl)urea (L1) and tris([(4-cyanophenyl)amino]propyl)thiourea (L2), have been synthesized and their anion binding properties have been investigated for halides and oxoanions. As investigated by 1H NMR titrations, each receptor binds an anion with a 1:1 stoichiometry via hydrogen-bonding interactions (NH⋯anion), showing the binding trend in the order of F− > H2PO4− > HCO3− > HSO4− > CH3COO− > SO42− > Cl− > Br− > I in DMSO-d6. The interactions of the receptors were further studied by 2D NOESY, showing the loss of NOESY contacts of two NH resonances for the complexes of F−, H2PO4−, HCO3−, HSO4− or CH3COO− due to the strong NH⋯anion interactions. The observed higher binding affinity for HSO4− than SO42− is attributed to the proton transfer from HSO4− to the central nitrogen of L1 or L2 which was also supported by the DFT calculations, leading to the secondary acid-base interactions. The thiourea receptor L2 has a general trend to show a higher affinity for an anion as compared to the urea receptor L1 for the corresponding anion in DMSO-d6. In addition, the compound L2 has been exploited for its extraction properties for fluoride in water using a liquid-liquid extraction technique, and the results indicate that the receptor effectively extracts fluoride from water showing ca. 99% efficiency (based on L2).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and anion binding studies of tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors: proton transfer-induced selectivity for hydrogen sulfate over sulfate

et al. 2015

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Solution Conformation and Self‐Assembly of Ferrocenyl(thio)ureas

et al. 2016

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Conformations and (dis)assembly processes of ureas and thioureas are of fundamental importance in supramolecular chemistry, anion binding, or crystal engineering, both in solution and in the solid state. For sensing and switching processes a redox-active unit, such as the ferrocene/ferrocenium couple, is especially suitable. Here, self-assembly processes of redox-active ferrocenyl(thio)ureas FcNHC(X)NHR [X = O, R = Fc (1), Ph (2), 1-naphthyl (3), Me (4), Et (5); X = S, R = Fc (6), 1-

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Chloride Encapsulation by a Tripodal Tris(4-pyridylurea) Ligand and Effects of Countercations on the Secondary Coordination Sphere

Zhang

Zhao

Wang

et al. 2014

Crystal Growth & Design

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A series of anion complexes of the 4-pyridyl-functionalized tripodal tris(urea) receptor (L) have been synthesized. Ligand L forms the 1:1 anion complex [Cl⊂L] − with various metal chloride salts, MCl x (M = Na, K, Mg, Ca, Mn, Co, x = 1 or 2). When M = Na, K, Mg, and Ca, the metal ions are not coordinated by the pyridyl groups of L but are involved in second-sphere coordination to form three-dimensional structures. However, in the complex of Co 2+ , the transition metal ions are directly coordinated by the pyridyl groups. Interestingly, the Mn 2+ ion forms two complexes with both of the above two types of structure. In all complexes, one chloride ion is "half" encapsulated in the cleft of one ligand by N−H•••Cl hydrogen bonds to form the [Cl⊂L] units, which are further linked via intermolecular interactions into three-dimensional structures. Moreover, the fluoride and carbonate complexes of L have also been obtained. The solution anion binding properties of L have been studied by 1 H NMR spectroscopy and electrospray ionization mass spectrometry.

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Anion Binding of a Protonated Tripodal Tris(ferrocenylurea) Receptor

Cited by 7 publications

References 66 publications

Synthesis and anion binding studies of tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors: proton transfer-induced selectivity for hydrogen sulfate over sulfate

Synthesis and anion binding studies of tris(3-aminopropyl)amine-based tripodal urea and thiourea receptors: proton transfer-induced selectivity for hydrogen sulfate over sulfate

Solution Conformation and Self‐Assembly of Ferrocenyl(thio)ureas

Chloride Encapsulation by a Tripodal Tris(4-pyridylurea) Ligand and Effects of Countercations on the Secondary Coordination Sphere

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