74568-07-3Relevant articles and documents
Mathematical modeling studies for the adsorptive removal of ciprofloxacin drug from water samples using functionalized silica resin
Elik, Mustafa,Jalbani, Nida Shams,Junejo, Ranjhan,Kaya, Savas,Serdaroglu, Goncagül
, (2022/02/14)
The current research demonstrates the adsorptive removal of ciprofloxacin antibiotic drug from pharmaceutical wastewater samples using functionalized silica (FS) resin through batch adsorption experiments. The adsorption experiments were performed under the optimized parameters such as pH effect, FS-resin amount, ciprofloxacin concentration, equilibrium time and temperature. Results demonstrate that the maximum adsorption of ciprofloxacin was achieved at pH (6.5), while the effective resin dose was 20?mg?L?1. The Langmuir and Freundlich models were applied on equilibrium data, and it has been observed that the adsorption was best fit to the Freundlich model with a good correlation coefficient (R2 = 0.999). Moreover, the thermodynamic and kinetic parameters show that the adsorption of ciprofloxacin is endothermic and spontaneous in nature followed by pseudo-second-order kinetic model. To explore the efficiency of resin, the real wastewater samples were collected and it has been observed that resin has better potential to treat pharmaceutical effluents. Furthermore, the FS-resin and ciprofloxacin interaction were analyzed at a molecular level through quantum chemical calculation. Graphical abstract: [Figure not available: see fulltext.]
Optimization of toxic metal adsorption on DEA-calix[4]arene appended silica resin using a central composite design
Gul, Samiha,Memon, Fakhar N.,Memon, Shahabuddin
, p. 3448 - 3463 (2022/02/21)
The present study is devoted to the application of Central Composite Design (CCD) to purify water contaminated with toxic metal ions (Pb2+, Cd2+ and Hg2+) using a p-tert-diethanolaminomethylcalix[4]arene (DEA-C4) based silica resin. The synthesized material was characterized using SEM, FTIR and EDX techniques. Three effective parameters (pH, adsorbent dosage and concentration of metal ion) were optimized by assessment with CCD. The data was analyzed using the quadratic model and the obtained results revealed the highest % adsorptions for Pb2+ (92.7), Cd2+ (93.7) and Hg2+ (88.2) at the optimum points for pH (5.4, 3.18 and 3.89), adsorbent dosage (23.8, 25.5 and 26.12 mg) and metal ion concentration (5.3, 7.62 and 7.18 ppm), respectively. Analysis of variance (ANOVA) results show a good fit for the regression model, showing R2 values of 0.99 for Pb2+, 0.99 for Cd2+ and 0.98 for Hg2+. Furthermore, the results from Freundlich adsorption isotherms suggest its favorability, as the values for n are >1 (i.e., 7.06, 8.85 and 13.2) and there are higher values for R2 = 0.97, 0.99 and 0.98 for Pb2+, Cd2+ and Hg2+, respectively. However, for the Langmuir isotherm, the value of the separation factor RL is >1 (1.01, 1.02 and 1.05 for Pb2+, Cd2+ and Hg2+, respectively), revealing its un-favorability. In kinetics, the pseudo-second-order kinetic model (Ho and McKay) shows R2 values of 0.998, 0.999 and 0.999 for Pb2+, Cd2+ and Hg2+, suggesting the chemical reaction seems significant in the rate controlling step. The thermodynamic results concluded that the reaction is spontaneous and exothermic in nature.
Joining a host-guest platform and a light-emission motif: Pyrazinamide-calixarene hybrids
Alvarenga, Meiry Edivirges,Alves, Rosemeire Brondi,Guimar?es, Freddy Fernandes,Lara, Thiago Vinicius Costa,Maia, Lauro June Queiroz,Martins, Felipe Terra,da Silva, Cleiton Moreira,de Santana, Ricardo Costa
, (2022/03/07)
Calixarenes are macrocyclic polyphenols widely used as hosts in supramolecular chemistry approaches. Recently, aminopyrazine has emerged as a high-efficiency blue light emitting moiety. Inspired by this knowledge, here we prepared two pyrazinamide-calixarene hybrids, in order to join in a single molecular platform both host-guest and light-emission properties. Both compounds were decorated with pyrazinamide at the upper rim, on two phenyl rings alternated into the four-units of the calixarene macrocycle. Their difference was the t?butyl substitution on the other two alternate phenyl rings. The t?butyl substituted derivative crystallized in two crystal forms, a non-solvated and a DMF mono-solvate phase, both with just one crystallographically independent hybrid molecule, while the compound without t?butyl moieties crystallized with three hybrid conformers and four DMF molecules. The molecular substitution pattern has also impacted on the crown conformation, being related to more inclined pyrazinamide-phenyl average planes in the absence of the t?butyl substituents. The coplanarity pattern between pyrazinamide and its bonded phenyl ring and the conformational profile of this substituent changed among the three conformers of derivative without the t?butyl group and between those assembling the two crystals forms of the other compound, which was also found in our DFT calculations. Under an excitation wavelength of 388 nm, a broad band emission between 400 nm and 550 nm was found for the three crystal forms, with maxima at ca. 500 nm, with low quantum yields of up to 0.4%. TD-DFT absorption spectra were overlaid to the experimental excitation spectra, while the low efficiency was rationalized both as an effect of the DMF guest and the tail-to-tail π…π stacking interactions between coplanar pyrazinamide-phenyl moieties of the centrosymmetric related molecules.
Reversible coloring/decoloring reactions of thermochromic leuco dyes controlled by a macrocyclic compound developer
Chaodongbung, Tawatchai,Kaewtong, Chatthai,Pattavarakorn, Datchanee,Saenkham, Audchara,Sriphalang, Sanguansak,Wanno, Banchob
, (2022/03/31)
In this study, we examine macrocyclic compounds to determine whether they can provide a safer replacement and stable complex for BPA in thermochromic dyes. To achieve this objective, a series of macrocyclic compounds, Methyl-N-benzylhexahomotriazacalix[3]arene (MeAC3), p-Chloro-N-benzylhexahomo-triazacalix[3]arene (ClAC3), α-Cyclodexdrin (α-CD), β-Cyclodexdrin (β-CD), p-tert-Butylthiacalix[4]arene (TC4), Calix[4]arene (C4), and Resorcin[4]arene (RC4), were synthesized. Among these macrocyclic compounds, RC4 was determined to be the most appropriate candidate to replace BPA as the developer material used in thermochromic dyes. In tests of prepared thermochromic dyes, RC4 had results similar to those of BPA, achieving the best protonation/deprotonation equilibria and providing a dark contrast with the thermochromic dye. DFT calculations also showed stable complexes between RC4 and CVL via hydrogen-bond interactions.
Synthesis of new calix[4]arene derivatives and evaluation of their cytotoxic activity
Oguz, Mehmet,Yildirim, Ayse,Durmus, Irem Mukaddes,Karakurt, Serdar,Yilmaz, Mustafa
, p. 52 - 59 (2021/11/03)
Since calixarenes are more easily synthesized and functionalized than other supramolecules, they are compounds of interest in organic chemistry. In this study, the dihydrazide (3a and 3b) and diamino propyl (6a and 6b) derivatives of p-tert-butylcalix[4]arene and calix[4]arene were synthesized. Then the L-proline methyl ester substituted chlorocyclopropenium was reacted with the calix[4]arene derivatives (3a, 3b, 6a, and 6b) at room temperature in CH2Cl2 to obtain calix[4]arene superbase derivatives (4a, 4b, 7a, and 7b) in 75%, 60%, 70%, and 55% yield, respectively. The synthesized compounds’ structure was elucidated using spectroscopic techniques (FTIR, 1H NMR, and 13C NMR). The cytotoxic properties of the calix[4]arene superbase derivatives were investigated against different human cancer cell, including A549, DLD-1, HEPG2, and PC-3 and human healthy epithelium cell line PNT1A. The cytotoxicity results showed that calix[4]arene superbase derivatives inhibited the proliferation of DLD-1, A549, HEPG2, and PC-3 cells in a dose-dependent manner. Compound 7a had the highest toxic effect on colorectal carcinoma (IC50: 4.7 μM), and the IC50 values were 18.5 μM and 74.4 μM against human prostate and lung cancer cells, respectively. Furthermore, compound 4b was found more effective on hepatocellular carcinoma cells (IC50: 210.2 μM). As a result, the synthesized calix[4]arene superbase derivatives can be developed to treat different human cancer cell. They can be considered as a preliminary result for molecular-level research. [Figure not available: see fulltext.]
Synthesis of new anthracene-substituted calix[4]triazacrown-5 as highly sensitive fluorescent chemosensor and extractant against hazardous dichromate anion
Sayin, Serkan
, p. 1716 - 1724 (2021/07/14)
A new fluorogenic anthracene functionalized calix[4]triazacrown-5 (Ant-AzClx) was successfully synthesized using a simple Schiff’s base reaction. The 1H-NMR, 13C-NMR, ESI-MS, and elemental analysis techniques were performed to characterize its structure. Excited at 370 nm, Ant-AzClx reveals excimer emission at 418 nm. Therefore, its anion binding properties were investigated against F?, HCO3?, H2PO4?, NO3?, Cr2O72?, and SO42? ions. When hazardous dichromate anion was introduced into medium, the fluorescence intensity of Ant-AzClx was markedly quenched. The binding constant, stoichiometry, the detection limits and Stern–Volmer equation for the complex formed between Ant-AzClx and Cr2O72? ion were determined. Furthermore, the 1H-NMR technique was also performed to assess the mechanism of the complex (Ant-AzClx@Cr2O72?). Apart from its excellent fluorescent chemosensor properties for selective and sensitive recognition of Cr2O72? ion, Ant-AzClx was used as an efficient extractant towards dichromate anion. The extraction results indicated that Ant-AzClx exhibited high extraction capability, leading to it being a promising extractant for the removal of dichromate anions from water.
IONOMERS WITH MACROCYCLIC MOIETIES FOR ION CONDUCTIVITY AND PERMSELECTIVITY
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Paragraph 00102, (2021/10/30)
Provided here are ion conducting materials including one or more macrocycles, and either one or more pendant groups or one or more backbone repeat units. The ion conducting materials exhibit distinctly high ion conductivity in thin film and bulk membrane
CALIXARENE COMPOUND, CURABLE COMPOSITION, AND CURED PRODUCT
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Paragraph 0132, (2021/07/02)
A calixarene compound represented by formula (1) below is provided. The calixarene compound contains, per molecule, at least one —CH2OH group or phenolic hydroxy group and at least one carbon-carbon unsaturated bond. R1's are a structural moiety (A), which has a —CH2OH group; a structural moiety (B), which has a carbon-carbon unsaturated bond; a structural moiety (C), which has a —CH2OH group and a carbon-carbon unsaturated bond; a monovalent organic group (D), which is different from (A), (B), and (C); or a hydrogen atom (E). R2's are (A), (B), (C), (D), or (E) provided that not all R2's are (E). R3's are one of a hydrogen atom, an aliphatic hydrocarbon group, and an aryl group. n is 2 to 10. * is a point of attachment to an aromatic ring. A curable composition including the calixarene compound is provided. A cured product of the curable composition is provided.
A Calix[4]arene-Based Cyclic Dinuclear Ruthenium Complex for Light-Driven Catalytic Water Oxidation
Noll, Niklas,Würthner, Frank
supporting information, p. 444 - 450 (2021/01/06)
A cyclic dinuclear ruthenium(bda) (bda: 2,2’-bipyridine-6,6’-dicarboxylate) complex equipped with oligo(ethylene glycol)-functionalized axial calix[4]arene ligands has been synthesized for homogenous catalytic water oxidation. This novel Ru(bda) macrocycle showed significantly increased catalytic activity in chemical and photocatalytic water oxidation compared to the archetype mononuclear reference [Ru(bda)(pic)2]. Kinetic investigations, including kinetic isotope effect studies, disclosed a unimolecular water nucleophilic attack mechanism of this novel dinuclear water oxidation catalyst (WOC) under the involvement of the second coordination sphere. Photocatalytic water oxidation with this cyclic dinuclear Ru complex using [Ru(bpy)3]Cl2 as a standard photosensitizer revealed a turnover frequency of 15.5 s?1 and a turnover number of 460. This so far highest photocatalytic performance reported for a Ru(bda) complex underlines the potential of this water-soluble WOC for artificial photosynthesis.
Ion sensing of sister sensors based-on calix[4]arene in aqueous medium and their bioimaging applications
Alizada, Malak,Gul, Alev,Kursunlu, Ahmed Nuri,Oguz, Mehmet,Yilmaz, Mustafa
, (2020/08/28)
Here, sister calix[4]arene derivatives containing two NBD (7-nitro-benzofurazan) units in 1,3-(distal) derivatives (sensors 4&8) were prepared and characterized by 1H, 13C NMR, FTIR, elemental analysis, and fluorescence spectroscopy. The ion binding properties of multi-channel sensors 4&8 were performed in the presence of various cations and anions. Both sensor compounds, 4&8, showed “on–off” type fluorescence response towards Cu2+ cation and H2PO4?&F? anions with high selectivity in aqueous solution (CH3CN/H2O, 4/1, v/v). The connected spectroscopic parameters were investigated as the complex stoichiometry, binding constant etc. for a better result. Moreover, the lowest detection limit of 4 for sensing Cu2+ and H2PO4?&F? were obtained 2.4 × 10?8, 9.1 × 10?7, 9.7 × 10?7 mol/L respectively. the lowest detection limit of Cu2+ and H2PO4?&F? by 8 was obtained as 2.9 × 10?8, 9.7 × 10?7, 8.9 × 10?7 mol/L respectively. The confocal microscope was performed to investigate the sensor properties of 4&8 towards ions on living cells. Sensors 4 and 8 showed fluorescence properties on the A549 cell line, while it was observed to turn off the fluorescence intensity in cells treated with H2PO4?, F? and Cu2+ ions. Besides, compounds 4 and 8 can be used to identify H2PO4?, F? and Cu2+ ions in living cells.
