Complexation and sensing of dicarboxylate anions and dicarboxylic acids

Curiel, David; Más‐Montoya, Miriam; Sánchez, Guzmán

doi:10.1016/j.ccr.2014.09.010

Cited by 80 publications

(29 citation statements)

References 222 publications

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“…[21] Specifically,t he hydrodynamic volume (V H )o f3-6 resulted to be 331 3 , which, on adding excess 1-12,increased to 685 3 .T he V H of 1-12,asmeasured by PGSE NMR, was 382 3 and 408 3 at 2mm and 30 mm,r espectively,d enoting an equilibration between + N À N + dications,and the corresponding monovalent + NÀN + ···I À and neutral I À ··· + NÀN + ···I À ion pairs. [23] These binding constants might be explained by as ize-matching effect, similar to the one observed in the solid state,which produces ap erfect electrostatic pairing between 1 and 3,t hus creating stable complexes also in solution (Figure 2). 19 FNMR titration experiments in [D 2 ]DCM: [D 4 ]MeOH (10:1) solution revealed an association constant of 12.1 AE 0.6 Lmol À1 for 1-10·3-4 and 19 AE 1Lmol À1 for 1-12·3-6.These values underline as trong association between salts 1 and diacids 3,w hich is higher than other hydrogen-bonded complexes involving similar dicarboxylic acids reported previously.…”

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confidence: 78%

Dicarboxylic Acid Separation by Dynamic and Size‐Matched Recognition in Solution and in the Solid State

et al. 2018

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Bis(trimethylammonium) alkane diiodides dynamically encapsulate dicarboxylic acids through intermolecular hydrogen bonds between the I anions of the hosts and the carboxylic OH groups of the guests. A selective recognition is realized when the size of the I ⋅⋅⋅HOOC(CH /CF ) COOH⋅⋅⋅I superanion matches the dication alkyl chain length. Dynamic recognition is also demonstrated in solution, where the presence of the size-matching organic salt boosts the acid solubility profile, thus allowing efficient mixture separation.

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confidence: 78%

Dicarboxylic Acid Separation by Dynamic and Size‐Matched Recognition in Solution and in the Solid State

et al. 2018

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“…Based on our previous studies of coordination polymers [5][6][7], constructing coordination complexes and polymers, from carboxylates and nitrogen-containing mixed ligands, has become our current interest. Among the most used bridging ligands for transition metal ions are dicarboxylate ligands [8]. In particular, malonate has been extensively used for the formation of coordination complexes [9] and coordination polymers [10].…”

Section: Introductionmentioning

confidence: 99%

1D and 3D supramolecular structures exhibiting weak ferromagnetism in three Cu(II) complexes based on malonato and di-alkyl-2,2’-bipyridines

Jaramillo-García

Téllez-López

Martínez-Domínguez

et al. 2016

Journal of Coordination Chemistry

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Escudero (2016) 1D and 3D supramolecular structures exhibiting weak ferromagnetism in three Cu(II) complexes based on malonato and di-alkyl-2,2'-bipyridines, Journal of Coordination Chemistry, 69:9, 1525-1540, ABSTRACTThree new Cu(II) complexes composed of malonato (mal), methylmalonato (memal), 4,4′-di-tert-butyl-2,2′-bipyridine (tbpy) and 5,5′-dimethyl-2,2′-bipyridine (mebpy) ligands, Cu(H 2 O)(mal)(tbpy) (1), Cu(H 2 O)(memal)(tbpy) (2) and Cu 4 (H 2 O) 4 (memal) 4 (mebpy) 4 ·11H 2 O (3) were synthesized by simple onepot solution reactions at ambient conditions. Single-crystal X-ray diffraction analyses reveal that the Cu(II) ions exhibit a distorted five-coordinate square pyramidal geometry. These three complexes display supramolecular arrays due to hydrogen-bonding interactions. Complexes 1 and 2 show 1-D supramolecular structures; 1 forms a double-ion chain, unlike 2, which only generates a single-ion chain. In 3, there are two identical monomers in the asymmetric unit with Z″ = 2; its high number of noncoordinated water molecules, along with hydrogen-bonding interactions between aqua ligand and memal ligand, generate a supramolecular tetramer, which mimics to produce a 3-D supramolecular framework. Besides this fascinating and yet uncommon crystallographic phenomenon in 3, the structural differences found in these complexes arise from the substituted groups in the malonato dianion and in the bipyridine ligands. These compounds exhibit weak ferromagnetic-exchange interactions. ARTICLE HISTORY

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“…To understand the earlier phenomena, the study of anion complexation to macrocyclic polyammonium cations (MCPACs) draws attention to researchers in the field of both chemistry and biology (Marecek et al ., ; Beer et al ., ; Sessler et al ., ; Llinares et al ., 2003; Curiel et al ., ) as they attempt to understand the molecular interactions involved in anion binding. MCPACs have therefore been reputed as anion complexones/receptors since Lehn's exploitation of them as anion‐recognizers (Graf and Lehn, ) because they are treated as to mimic of biological polyamines and can readily form complexes with anions in biological and nonbiological systems.…”

Section: Introductionmentioning

confidence: 99%

Recognition of silver nanoparticles surface‐adsorbed citrate anions by macrocyclic polyammonium cations: a spectrophotometric approach to study aggregation kinetics and evaluation of association constant

Choudhury

Purkayastha

Debnath

et al. 2016

J of Molecular Recognition

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In this report, we have studied the recognition of citrate anions adsorbed on the surface of silver nanoparticles (cit-Ag-NPs), by macrocyclic polyammonium cations (MCPACs): Me6 [14]ane-N4 H8 (4+) (Tet-A/Tet-B cations) and [32]ane-N8 H16 (8+) , which are well reputed anion recognizers and are treated as to mimic of biological polyamines. The study was monitored on ultraviolet-visible spectroscopy by performing a titration of the aqueous dispersion of the cit-Ag-NPs by the aqueous solution of MCPACs. The ultraviolet-visible time-scan plots over the reduction of the absorption band of surface plasmon resonance of cit-Ag-NPs at 390 nm are well fitted with fourth-order polynomial equation and are employed to determine the initial aggregation rate constants. It has been stated that the aggregation is the result in electrostatic attraction followed by H-bond formation between the surface-adsorbed citrate anions and added MCPACs. The atomic force microscopy results have evidenced aggregation of cit-Ag-NPs in presence of MCPACs. The evaluated H-bonded association constant (Kasso ) using Benesi-Hildebrand method reveals that [32]ane-N8 H16 (8+) cations form stronger association complex, as expected, with the citrate anions than the Me6 [14]ane-N4 H8 (4+) cations. The study would thus provide the insight of molecular interactions involved in nanoparticle surface-adsorbed anions with biological polyamines. Copyright © 2016 John Wiley & Sons, Ltd.

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Complexation and sensing of dicarboxylate anions and dicarboxylic acids

Cited by 80 publications

References 222 publications

Dicarboxylic Acid Separation by Dynamic and Size‐Matched Recognition in Solution and in the Solid State

Dicarboxylic Acid Separation by Dynamic and Size‐Matched Recognition in Solution and in the Solid State

1D and 3D supramolecular structures exhibiting weak ferromagnetism in three Cu(II) complexes based on malonato and di-alkyl-2,2’-bipyridines

Recognition of silver nanoparticles surface‐adsorbed citrate anions by macrocyclic polyammonium cations: a spectrophotometric approach to study aggregation kinetics and evaluation of association constant

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