Bis(crown ethers) derived from biphenyl: extraction and electrochemical properties

Costero, Ana M.; Sanchis, Joaquı́n; Peransi, Sergio; Gil, Salvador; Sanz, Vicente Claramonte; Doménech, Antonio

doi:10.1016/j.tet.2004.03.065

Cited by 27 publications

(10 citation statements)

References 19 publications

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“…Many of the benefits of crown ethers can be traced to their ability to encapsulate metal cations in their cyclic cavity, with a metal cation selectivity that at a simplistic level depends on the best-fit cation radius/crown ring size scenario. [13] There is a wealth of crown polycycles, [14] and numerous binding studies have been preformed using NMR spectroscopy, [15] potentiometric titrations, [16] bi-layer extraction, [17] redox response alterations [18] and luminescence quenching. [19] In particular, the simple polyethers C4-C6 have been described by Bartsch, [20] Changrong, [21] Reinhoudt [22] and Bouzide, [23] although metal ion binding has been reported only by Yakshin et al [24] This latter report concentrated on the cationextraction properties of this class of polyether.…”

Section: Introductionmentioning

confidence: 99%

A Strategy for Controlling the Central Torsion Angle in Biphenyl‐Based Molecular‐Scale Bridges

et al. 2005

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The synthesis of a series of crown ether ligands (C4-C6) based upon the 2,2Ј-biphenyl unit is described. In the series, the length of the polyether chain connecting the two oxygen atoms increases progressively. These polyethers are moderately fluorescent in acetonitrile solution, but this emission is partially quenched upon the addition of various alkali metal cations. Spectrofluorimetric titrations performed with MClO 4 (M = Li + , Na + ) or KPF 6 show that binding to crown ethers C4-C6 involves the formation of a 1:1 cation/ligand complex.

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Section: Introductionmentioning

confidence: 99%

A Strategy for Controlling the Central Torsion Angle in Biphenyl‐Based Molecular‐Scale Bridges

et al. 2005

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“…This compound was converted into the corresponding acyl chloride by treatment with thionyl chloride. 5 Diamide 1 was obtained after reaction with compound 4. Colorimetric recognition of F -has been a topic of interest during the last years and there are many systems able to act as sensors for this anion.…”

Section: Resultsmentioning

confidence: 99%

“…UV spectra were run at 20ºC (thermostated) on a Shimadzu UV-2102 PC Synthesis of N,N'-bis[3-oxa-pentyl-5-(5-nitro-2-(4-nitro-2-methyl benzoate) benzoate)]-2,6-pyridine dicarboxamide (1). 2-(2-methyloxycarbonyl-4-nitrophenyl)-5-nitrobenzoic acid 5 (0.5050 g, 1.46 mmol) was added to an excess of thionyl chloride (30 ml). The suspension was refluxed under magnetic stirring until it became a clear solution (2 h).…”

Section: Methodsmentioning

confidence: 99%

Colorimetric sensing of anions by a neutral biphenyl based amide receptor

Costero

Peransi²

2006

Arkivoc

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A new colorimetric sensor for fluoride is described. Compound 1 shows an open structure and its behaviour is compared with that of two related closed compounds 2 and 3. In all cases, the red colour developed in the presence of fluoride can be related to deprotonation processes, however ligand 1 gives rise to a faster colour change than 2 or 3 because of its higher flexibility. Other halides as well as carboxylates have been studied and the stoichiometry and complexation constants for the corresponding ligands have been determined.

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“…Their generic name originates from their molecular shape, reminiscent of a royal crown [3]. Because of their selective complex formation with hard metal ions as well as their negligible water solubility, crown ethers have been extensively used as suitable ion-carriers in solvent-solvent and solid phase extractions [4][5][6][7], ion-transport [8][9][10], ion-selective and PVC membrane ion-selective electrode studies [11][12][13], and the crown ether complexes were applied as a nano-switch recently [14][15][16].…”

Section: Introductionmentioning

confidence: 99%

QSPR probing of Na+ complexation with 15-crown-5 ethers derivatives using artificial neural network and multiple linear regression

Daraei

Irandoust

Ghasemi

et al. 2011

J Incl Phenom Macrocycl Chem

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A quantitative structure-property relationship (QSPR) study is performed to develop a model, relating to Na ? complex stability constant (log K) and the structure of 74 derivatives of 1,4,7,10,13-pentaoxacyclo-pentadecane ethers (15C5). Stepwise Multiple Linear Regression (SMLR) and Artificial Neural Network (ANN) methods have been exploited as linear and nonlinear methods, respectively to build the QSPR model. MOPAC software embedded in ChemOffice 2004 package was used for the minimizing energy using semi-empirical AM1 method. The optimum structures have been applied to generate more than 50 descriptors using available servers in ChemOffice 2004. The five most important constitutional, steric, electronic, thermodynamic and molecular descriptors were selected using the common preselection method combined by SMLR method. SMLR and ANN models were constructed based on the five selected descriptors. Both proposed models efficiently predict log K of 15C5 complexes. However, the results of ANN were more effective respect to SMLR model. This phenomenon reveals that log K of 15C5 complexes have a deviation from linear behavior related to the selected descriptors.

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Bis(crown ethers) derived from biphenyl: extraction and electrochemical properties

Cited by 27 publications

References 19 publications

A Strategy for Controlling the Central Torsion Angle in Biphenyl‐Based Molecular‐Scale Bridges

A Strategy for Controlling the Central Torsion Angle in Biphenyl‐Based Molecular‐Scale Bridges

Colorimetric sensing of anions by a neutral biphenyl based amide receptor

QSPR probing of Na+ complexation with 15-crown-5 ethers derivatives using artificial neural network and multiple linear regression

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