60835-71-4Relevant academic research and scientific papers
Cooperative Transport and Selective Extraction of Sulfates by a Squaramide-Based Ion Pair Receptor: A Case of Adaptable Selectivity
Dobrzycki, ?ukasz,Karbarz, Marcin,Romański, Jan,Wilczek, Marcin,Zaleskaya, Marta
, p. 13749 - 13759 (2020)
The use of a squaramide-based ion pair receptor offers a solution to the very challenging problem of extraction and transport of extremely hydrated sulfate salt. Herein we demonstrate for the first time that a neutral receptor is able not only to selectively extract but also to transport sulfates in the form of an alkali metal salt across membranes and to do so in a cooperative manner while overcoming the Hofmeister bias. This was made possible by an enhancement in anion binding promoted by cation assistance and by diversifying the stoichiometry of receptor complexes with sulfates and other ions. The existence of a peculiar 4:1 complex of receptor 2 with sulfates in solution was confirmed by UV-vis and 1H NMR titration experiments, DOSY and DLS measurements, and supported by solid-state X-ray measurements. By varying the separation technique and experimental conditions, it was possible to switch the depletion of the aqueous layer into extremely hydrophilic or less lipophilic salts, thus obtaining the desired selectivity.
Influence of Aryl-bonded Substituents on Complex Formation of Benzocrown Ethers with Alkali Metal Ions in Methanol and Acetone Solutions
Trueltzsch, Rainer,Beger, Joerg,Wolf, Gert,Buschmann, Hans-Juergen
, p. 5 - 10 (1994)
The influence of aryl-bonded substituents upon the complex formation of monobenzocrown ethers towards alkali metal ions in methanol and acetone solutions are investigated by using calorimetric and potentiometric titration.A different complexation behaviour of the ligands in acetone and methanol was found.In the case of the 1:1 complexation of Na+ a correlation between substituent effects and stability constants in acetone was noticed, however, the influence of substituents upon complex stability is weak.In methanol solutions no similar correlation could be established.During sandwich complexation of K+ in methanol, no significant substituent influences on K1 and K2 were observed.On the other hand, a considerable increase of ΔH2 for both the electron accepting and electron releasing substituents was found, probably caused by changes in ligand-cation solvation due to the substituents.
DESALINATION OF WATER USING A COMPLEXING AGENT ATTACHED TO A MAGNETIC NANOPARTICLE
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Page/Page column 89, (2022/03/09)
There is disclosed, a desalination apparatus making use of a particles including covalently bonded functionalized magnetic nanoparticles coupled to a complexing agent. For example, the complexing agent may include a crown ether. The particles are optionally used for removing salt from water, for example sea water. The apparatus optionally includes a magnet for magnetic filtering, concentrating and/or removing the particles and/or contaminant (e.g., salt). In some embodiments, the salt is then separated back from the particles using UV light. The remaining unclarified water may be washed out with the contaminant and/or used for salt production and/or disposed of (e.g., dumped back to the sea). Optionally, the particles are regenerated. For example, the regenerated particulars may be reused for further desalination steps (e.g., further salt removal from the clarified water) to clarify new input water. Covalently bonded functionalized magnetic nanoparticles coupled to a complexing agent are also disclosed.
Tripodal, squaramide‐based ion pair receptor for effective extraction of sulfate salt
Jagleniec, Damian,Romański, Jan,Wilczek, Marcin
, (2021/05/28)
Combining three features—the high affinity of squaramides toward anions, cooperation in ion pair binding and preorganization of the binding domains in the tripodal platform—led to the effective receptor 2. The lack of at least one of these key elements in
Chalcogen Bond Mediated Enhancement of Cooperative Ion-Pair Recognition
Bunchuay, Thanthapatra,Docker, Andrew,Eiamprasert, Utt,Surawatanawong, Panida,Brown, Asha,Beer, Paul D.
supporting information, p. 12007 - 12012 (2020/05/18)
A series of heteroditopic receptors containing halogen bond (XB) and unprecedented chalcogen bond (ChB) donors integrated into a 3,5-bis-triazole pyridine structure covalently linked to benzo-15-crown-5 ether motifs exhibit remarkable cooperative recognition of halide anions. Multi-nuclear 1H, 13C, 125Te and 19F NMR, ion pair binding investigations reveal sodium cation–benzo-crown ether binding dramatically enhances the recognition of bromide and iodide halide anions, with the chalcogen bonding heteroditopic receptor notably displaying the largest enhancement of halide binding strength of over two hundred-fold, in comparison to the halogen bonding and hydrogen bonding heteroditopic receptor analogues. DFT calculations suggest crown ether sodium cation complexation induces a polarisation of the sigma hole of ChB and XB heteroditopic receptor donors as a significant contribution to the origin of the unique cooperativity exhibited by these systems.
Recognition and Extraction of Sodium Chloride by a Squaramide-Based Ion Pair Receptor
Jagleniec, Damian,Siennicka, Sylwia,Dobrzycki, ?ukasz,Karbarz, Marcin,Romański, Jan
, p. 12941 - 12952 (2018/10/15)
We synthesized an ion pair receptor 1 consisting of a crown ether cation binding site and a squaramide anion binding domain and compared its binding properties to those of its analogous urea counterpart 2. We studied their salt binding properties using spectrophotometric and spectroscopic measurements in an acetonitrile solution and in acetonitrile/water mixtures. Apart from carboxylate anions, all of the anions tested were found to associate with receptor 1 and 2 more strongly in the presence of sodium cations. A homotopic anion receptor 3, lacking a crown ether unit, was unable to bind sodium salt more strongly than tetrabutylammonium salts. Solution and solid-state X-ray measurements revealed strong sodium chloride coordination to receptor 1, which is able to bind this salt even in the presence of 10% water. In contrast to the urea-based ion pair receptor 2 or anion receptor 3, ditopic receptor 1 is capable of extracting sodium chloride from aqueous media to the organic phase, as was evidenced unambiguously by 1H nuclear magnetic resonance, mass spectrometry, and atomic absorption spectroscopy analyses.
Production of macrocyclic polyether benzo-15-crown-5 and its functional derivatives
Glushko, Valentina N.,Sadovskaya, Natalya Yu.,Kozhuhov, Vadim I.,Blokhina, Lidiya I.,Antropova, Irina A.,Petina, Ekaterina S.,Retiviov, Vasiliy M.,Melnikova, Ekaterina Yu.
, p. 1689 - 1697 (2017/10/27)
Study of interaction between catechol and tetraethylene glycol dichloride in the n-butanol media, resulting with benzo-15-crown-5 production. Production of nitro- and amino-derivatives of benzo-15-crown-5. Determination of their thermogravimetric characteristics.
Tautomeric chromoionophores derived from 1-aryloxyanthraquinones and 4′-aminobenzo-15-crown-5 ether: Sandwich complex formation enhanced by interchromophoric interactions
Martyanov, Timofey P.,Klimenko, Lubov S.,Kozlovskiy, Viacheslav I.,Ushakov, Evgeny N.
, p. 681 - 691 (2017/01/16)
A series of tautomeric chromoionophores were prepared photochemically from 1-aryloxyanthraquinones and 4′-aminobenzo-15-crown-5 ether. All the synthesized dyes can bind strontium and barium cations as sandwich-type 2:1 ligand–metal complexes that show higher stability constants (K2:1) than the corresponding 1:1 complexes (K1:1), the K2:1/K1:1ratio reaching a value of 10 (in MeCN). The inverse relation, i.e. K2:1?1:1, is observed for the related complexes of unsubstituted benzo-15-crown-5 ether. The sandwich complexes were studied by spectrophotometry,1H NMR spectroscopy, mass spectrometry, and density functional theory calculations. A correlation was found between the K2:1/K1:1ratio and the number of short stacking contacts in the sandwich complex.
Synthesis and properties of macroheterocyclic azomethines based on 4-aminobenzo-15-crown-5
Sadovskaya, N. Yu.,Glushko,Retivov,Belus',Grokhovskii
, p. 2771 - 2777 (2016/02/18)
A number of new stable azomethine crown ether derivatives have been synthesized by condensation of 4-aminobenzo-15-crown-5 with aromatic aldehydes. Complexation of the products with transition metal cations (Cu2+, Zn2+, Fe3+, Co3+, Ni3+) has been studied by spectrophotometry.
Supramolecular assembly of isocyanorhodium(i) complexes: An interplay of rhodium(i)···rhodium(i) interactions, hydrophobic-hydrophobic interactions, and host-guest chemistry
Chan, Alan Kwun-Wa,Wong, Keith Man-Chung,Yam, Vivian Wing-Wah
, p. 6920 - 6931 (2015/06/16)
A series of tetrakis(isocyano)rhodium(I) complexes with different chain lengths of alkyl substituents has been found to exhibit a strong tendency toward solution state aggregation upon altering the concentration, temperature and solvent composition. Temperature- and solvent-dependent UV-vis absorption studies have been performed, and the data have been analyzed using the aggregation model to elucidate the growth mechanism. The aggregation is found to involve extensive Rh(I)···Rh(I) interactions that are synergistically assisted by hydrophobic-hydrophobic interactions to give a rainbow array of solution aggregate colors. It is noted that the presence of three long alkyl substituents is crucial for the observed cooperativity in the aggregation. Molecular assemblies in the form of nanoplates and nanovesicles have been observed in the hexane-dichloromethane solvent mixtures, arising from the different formation mechanisms based on the alkyl chain length of the complexes. Benzo-15-crown-5 moieties have been incorporated for selective potassium ion binding to induce dimer formation and drastic color changes, rendering the system as potential colorimetric and luminescent cation sensors and as building blocks for ion-controlled supramolecular assembly.
