- Preparation of the ferrocene-substituted 1,3-distal p-tert-butylcalix[4]arene based QCM sensors array and utilization of its gas-sensing affinities
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The article describes the synthesis of the new ferrocene-substituted calix[4]arene derivative 4 as sensitive layer, and suggests that the immobilization of it is on a quartz crystal microbalance gold electrode via the drop-casting method in order to produce the calix[4]arene-based QCM sensor. In addition, sensor response of the calix[4]arene-based QCM sensor was investigated towards carbon dioxide (CO2) and carbon monoxide (CO). The sensing and selectivity studies show that the ferrocene-substituted calix[4]arene-based QCM sensor is an effective gas sensor toward both carbon dioxide and carbon monoxide.
- Sayin, Serkan,Ozbek, Cebrail,Okur, Salih,Yilmaz, Mustafa
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- Synthesis of environmentally friendly, efficient and highly recyclable Lewis acid-type calix[4]arene catalysts containing flexible or bulky groups for the Mannich reaction
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Two new calix[4]arene-based Lewis acid-type catalysts containing flexible and bulky groups (2 and 3) were successfully synthesized. Their structures were characterized using FTIR, 1H-NMR, COSY-NMR, 13C-NMR, APT-NMR, and elemental ana
- Sayin, Serkan,Yilmaz, Mustafa
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- Feeding a Molecular Squid: A Pliable Nanocarbon Receptor for Electron-Poor Aromatics
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A hybrid nanocarbon receptor consisting of a calix[4]arene and a bent oligophenylene loop ("molecular squid"), was obtained in an efficient, scalable synthesis. The system contains an electron-rich cavity with an adaptable shape, which can serve as a host
- Bury, Wojciech,Cybińska, Joanna,Frydrych, Rafa?,Lis, Tadeusz,St?pień, Marcin
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- Columnar self-assembly, gelation and electrochemical behavior of cone-shaped luminescent supramolecular calix[4]arene LCs based on oxadiazole and thiadiazole derivatives
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A new class of blue light-emitting supramolecular liquid crystalline cone or bowl-shaped compounds were synthesized from substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles inbuilt with ester groups containing substituted alkoxy side chains (-OC4H9,-OC8H17) at the lower rim of calix[4]arene. These supramolecular compounds were investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), high-temperature X-ray diffraction (XRD), cyclic voltammetry (CV) and photophysical behavior studies. It was observed that the 1,3,4-thiadizole calix[4]arene-based derivatives are more capable of stabilizing the hexagonal columnar phase over a broad thermal range compared to the 1,3,4-oxadiazole calix[4]arene derivatives. The cone-shaped calixarene-based LCs with terminally substituted alkyl chains are packed into columns with enhanced intermolecular interactions. Moreover, the 1,3,4-oxadiazole calix[4]arene derivatives show deeper blue emissions compared to the 1,3,4-thidiazole calix[4]arene derivatives in solution as well as in thin films. The thermal and photophysical behaviors of the synthesized bowl-shaped supramolecular derivatives are extremely dependent on the terminal substituted alkoxy chains on the lower rim of calix[4]arene. Due to their hexagonal columnar phases and the emissive nature of their supramolecular liquid crystal and xerogel states, these molecules are favourable for application in emissive electronic displays. The 1,3,4-thiadiazole calix[4]arene derivatives display lower band gaps than the 1,3,4-oxadiazole calix[4]arene derivatives and are considered to be promising entities for applications in organic light emitting diodes (OLEDs).
- Sharma, Vinay S.,Shah, Akshara P.,Sharma, Anuj S.,Athar, Mohd
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- Fabrication of calixarene based protein scaffold by electrospin coating for tissue engineering
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In this study, calixarene was synthesized by using different functional groups as p-tert-butyl- Calix[4]arene ester and amides. Calixarene nanofibers were produced by electrospin coating. Protein immobilization onto the calixarene nanofibers was carried out with human serum albumin (HSA). The maximum amount of binding on produced three different calixarene nanofibers (DE, 2-AMP and 3-AMP) was compared by using a fluorescence technique for protein analysis. Result showed that maximum binding amount was found to be as 177.85 mg cm-2 for 3-AMP surface. The protein binding was also characterized by using SEM, TEM, AFM and FT-IR. From obtained results, calixarene-albumin nanofiber was also fabricated by spin coating using 3-AMP which has ability max binding of protein.
- Cagil, Esra Maltas,Ozcan, Fatih,Ertul, Seref
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- Preparation and Application of Chemically Bonded Silica Supported Calix[4]arene as Reinforced Filler in NR/BR Blend Based Rubber Compounds
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In this study, we tried to reduce polarization of silica surface by chemically bonding cholorosulfonyl calix[4]arene (CSC[4]A) and silica (Si–O–Cl) to improve dispersion between filler and elastomer. To confirm synthesis of CSC[4]A, 1H NMR, 13C NMR, and IR spectrophotometry were used. Obtained composite of chemically bonded silica and CSC[4]A was characterized by TGA. Compounds (contained silica, silica and silane, silica-calix system) were prepared to investigate the effect of silica-calix system (CSC[4]A-SiO2) on the rheological and mechanical properties of rubber compounds based on natural rubber/cis-butadiene rubber (NR/BR) blend in tire tread formulation. The rheological and mechanical properties of three samples were investigated by different devices and a surface morphology was evaluated by FESEM technique. The results revealed that the curing behavior of the compound with CSC[4]A-SiO2 did not significantly differ from other compounds, while reversion was considerably reduced compared with that to other compounds. Also, the mechanical properties of compound with CSC[4]A-SiO2 were improved dramatically especially in fatigue resistance.
- Mohamadi, Hediye,Motiee, Fereshte,Saber Tehrani, Mandana,Taghvaei-Ganjali, Saeed
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- Preparation of thermosensitive, calix[4]arene incorporated P(NIPAM-co-HBCalix) hydrogel as a reusable adsorbent of nickel(II) ions
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A calix-conjugated thermo-responsive hydrogel containing 15% tetra(5-hexenyloxy)-p-tert-butylcalix[4]arene (HBCalix), P(NIPAM-co-HBCalix), was used to remove nickel(II) ions from water. Both thermo-sensitive properties and the Ni2+-adsorption capabilities of the prepared P(NIPAM-co-HBCalix) hydrogels are investigated. Introduction of the monomer HBCalix considerably enhanced the adsorption of Ni2+ onto the hydrogel by chelation between hexenyloxy groups and metal ion. When HBCalix units capture Ni2+ and forms HBCalix/Ni2+ host-guest complexes, the lower critical solution temperature of the hydrogel shifts to a higher temperature due to both the repulsion between charged HBCali/Ni 2+ groups and the osmotic pressure within the hydrogel. Adsorption studies were carried out by varying contact time, counter ion and initial concentration of Ni2+. The evaluation of adsorption properties showed that the hydrogel exhibited better correlation with Langmuir isotherm model. P(NIPAM-co-HBCalix) could be used repeatedly with little loss in adsorption capacity by simply changing the environmental temperature. This kind of ion-recognition hydrogel is promising as a novel adsorption material for adsorption and separation of Ni2+ ions.
- Yan, Fanyong,Wang, Meng,Cao, Donglei,Guo, Shanshan,Chen, Li
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- Application of sulfonamide derivative of calixarene for improvement of mechanical properties and thermal stability of polyurethane composite
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A calixarene derivative, 5,11,17,23-tetrakis (hydroxyl ethyl sulfonamide) calix[4]arene, was synthesized through a linear reaction from parent calix[4]arene. This sulfonamide calixarene derivative was used as a precursor to produce calixarene-polyurethane composite. Structural properties of calixarene-based synthesized precursors were studied using spectroscopic techniques such as 1H-NMR, 13C-NMR, and IR. Also, mechanical properties of produced polyurethane composite such as fracture elongation, modulus, and tensile strength were studied which indicated that these properties were deeply dependent upon calixarene ratio in composite. An increase in calixarene ratio resulted in a decrease the fracture elongation. In contrast, an increase in calixarene ratio caused a considerable decrease of modulus and tensile strength. The modulus and tensile strength were increased by 16.98 and 20 % as the calixarene/polyol ratio reached 3 %. Finally, TGA and DSC studies showed that calixarene ratio considerably enhanced the thermal stability of polyurethane.
- Taghvaei-Ganjali, Saeed,Rasouli-Saniabadi, Mona,Mirmoeini, Maryam Sadat
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- Synthesis of macrocyclic polyphenol resin by methylene crosslinked calix[4]arene (MC-[4]H) for the adsorption of palladium and platinum ions
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A novel macrocyclic polyphenol resin, a calix[4]arene derivative, namely, a methylene crosslinked calix[4]arene (MC-[4]H), was successfully synthesised by demethylation of MC-[4]CH3. MC-[4]CH3 was prepared by crosslinking [4]CH3 with s-trioxane under acidic conditions. Methylation of calix[4]arene ([4]H) is strongly required to protect the oxygen atoms on the phenolic groups. It was found that the adsorption of palladium and platinum optimally occurred at low pH. The maximum loading capacity of palladium on the resin was found to be 0.41 mol kg-1 while that of platinum was 0.23 mol kg-1. The stoichiometries of metal ions were found to be 5:1 of the calix[4]arene unit in MC-[4]H to Pd(ii) and 3:1 of that in MC-[4]H to Pt(iv), respectively.
- Priastomo, Yoga,Morisada, Shintaro,Kawakita, Hidetaka,Ohto, Keisuke,Jumina
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- Synthesis of p-tert-butylcalix[4]arene derivatives with trans-alkyl substituents on opposite methylene bridges
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Reaction of the bis(spirodiene) calixarene derivative 9 possessing exocyclic double bonds with tetraethylammonium fluoride or chloride afforded bis(spirodienone) calixarene derivatives substituted by the corresponding halogen atoms (11 and 12). Reaction of 9 with alkyl cuprates yielded in one step p-tert-butylcalix[4]arene derivatives with opposite methylene groups substituted in a trans fashion by identical alkyl substituents (methyl, ethyl, or isopropyl). The isopropyl derivative 16 displayed the largest cone-to-cone inversion barrier of the series.
- Simaan, Samah,Biali, Silvio E.
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- Effective Removal of the Direct Black-38 Dye from Wastewater Using a New Silica-Modified Resin: Equilibrium and Thermodynamics Modeling Studies
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In this study, the synthesis of p-diethanolaminomethylcalix[4]arene and its immobilization on a silica surface have been performed for the removal of the direct black (DB-38) dye from wastewater samples. The newly synthesized p-diethanolaminomethylcalix[4]arene-immobilized silica (DIS) resin has been analyzed and characterized by FTIR spectroscopy and SEM techniques. To check the efficiency of the DIS resin, batch and column adsorption procedures have been applied under the optimized parameters, i.e., resin dosage, pH, and temperature. To validate the experimental data, Langmuir, Freundlich, and D-R models have been applied. The results show that adsorption follows the Freundlich model well with a good correlation coefficient (R2 = 0.999). Moreover, the energy E (kJ/mol) was calculated with the help of the D-R model, which suggested that the adsorption has an ion exchange nature. The DIS resin was also applied to real industrial samples of DB-38 dye wastewater. The results show that the DIS resin removes 99% of the dye successfully. Thermodynamics studies were conducted to know the feasibility and the mechanism of the adsorption reaction. The thermodynamic parameters show that the adsorption is spontaneous and exothermic. The theoretical calculation was performed at the B3LYP/DZP calculation level of the ADF program, and the power of the interaction between adsorbent and dye molecules can be determined in the light of chemical reactivity analysis.
- Junejo, Ranjhan,Memon, Shahabuddin,Kaya, Savas
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- Delayed lanthanide luminescent Tb(III) complexes formed from lower rim amide functionalised calix[4]arenes
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The synthesis and the photophysical studies of a new generation of time resolved luminescent systems based on calix[4] arenes alkylated at the lower rim, capable of hosting lanthanide (III) ions such as terbium and sensitising its emission, are described. Two series of ligands were designed to provide an ideal cavity to host terbium (Tb(III)) and were synthesised in high yields following two novel approaches. The tetra-alkylation, which was achieved in one step using with piperidino- and morpholino-acetamide pendant arms, provides eight donor atoms forming a binding 'pocket' at an ideal distance from the metal core to favour the sensitisation via the antenna effect. Of the two ligand series developed, compounds 3 and 4 possess a short spacer between the calix and the amide receptor site. The second series of ligands 6-7, designed with longer pendant amide arms, was synthesised from 2 in two steps through the ester analogue 5. The crystal structure of 3 (and 6 as shown in Supporting Information, available online) is presented. The synthesis and the photophysical studies of the four resulting complexes 3.Tb, 4.Tb, 6.Tb and 7.Tb are described in detail and in each case, successful sensitisation of the terbium emission occurred upon excitation of the phenolic scaffold of the calixarene.
- Lincheneau, Christophe,Quinlan, Eoin,Kitchen, Jonathan A.,McCabe, Thomas,Matthews, Susan E.,Gunnlaugsson, Thorfinnur
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- Luminescent Calix[4]arene-based metallogel formed at different solvent composition
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We have synthesized a calix[4]arene derivative (1) containing terpyridine and showed that gelation occurred in the presence of Pt2+ in DMSO/H2O of varying compositions. Gelation was presumably mediated by the Pt-Pt and π-π stacking interactions. The scanning electron microscopy image of the xerogel showed a spherical structure with diameter of 1.8-2.1 μm. Interestingly, the metallogel showed strong luminescence enhancement, which was dependent on the DMSO/H2O ratio of the solvent. We examined the effects of concentration, temperature, and time resolution on the luminescence emission of both the gel 1-Pt2+ and the sol 1-Pt 2+. The luminescence lifetimes of the metallogel were particularly long, on the order of several microseconds. The luminescence lifetimes were also strongly dependent on the solvent composition. We also determined the thermodynamic parameters for the self-assembly of the gel by the Birks kinetic scheme. Furthermore, the rheological properties of the metallogels in the presence of more than 4.0 equiv of Pt2+ were independent of the concentration of Pt2+ applied.
- Park, Jaehyeon,Lee, Ji Ha,Jaworski, Justyn,Shinkai, Seiji,Jung, Jong Hwa
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- Synthesis, spectral characterisation and thermal behaviours of some new p-tert-butylcalix[4]arene and calix[4]arene-esters containing acryloyl groups
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The mono-, di-, tri-, and tetra-acryloyl esters of p-tert-butylcalix [4]arene and calix[4]arene were synthesised by reacting acryloyl chloride with sodium salts of p-tert-butylcalix[4]arene and calix[4]arene in THF. The structures of these compounds were characterised by IR, UV-VIS, 1H NMR, and 13C NMR. Thermal behaviour of the compounds were also examined by means of differential thermal analysis (DTA), thermogravimetry (TG), and derivative thermogravimetry (DTG).
- ?zkinali, Sevil,Kocaokutgen, Hasan
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- p-Nitro-tetradecyloxy-calix[4]arene as a highly selective stationary phase for gas chromatographic separations
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Here, we report the first example of the utilization of p-nitro-tetradecyloxy-calix[4]arene (C4A-NO2) as a stationary phase for capillary gas chromatographic (GC) separations. The statically coated C4A-NO2 column exhibited a high column efficiency of 3815 plates per m and moderate polarity. The C4A-NO2 column was investigated for its separation performance and retention behaviours by utilizing a wide variety of isomer mixtures, covering alkylated benzenes and naphthalenes, alkenes, furans, alcohols, benzaldehydes, phenols and halogenated anilines. Importantly, the C4A-NO2 column exhibited high resolving capability for both aliphatic and aromatic isomers. Particularly, it displayed advantageous resolving capability over the commercial DB-17 column for halogenated aniline isomers. This work provides a good reference for designing calixarene derivatives as GC stationary phases, which is important for developing a family of stationary phases with specific selectivity.
- Sun, Tao,Shuai, Xiaomin,Bin, Li,Ren, Kaixin,Jiang, Xingxing,Chen, Haipeng,Hu, Shaoqiang,Cai, Zhiqiang
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- Thermodynamic and Kinetic Studies for Adsorption of Reactive Blue (RB-19) Dye Using Calix[4]arene-Based Adsorbent
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A current study demonstrates the removal of Reactive Blue 19 (RB-19) from industrial wastewater by synthesizing p-piperdinocalix[4]arene-immobilized silica resin (PASR). The surface morphology and functional group analysis were performed with scanning electron microscopy and Fourier transform infrared spectroscopy. The dye removal efficiency of PASR was analyzed through adsorption studies. Different parameters were optimized such as the pH value of dye, amount of resin, concentration of dye, and effect of electrolyte on adsorption. The adsorption mechanism was analyzed with Langmuir, Freundlich, and Dubinin-Radushkevich (D-R) isotherms. It was found that experimental data follow the Freundlich isotherm, which suggests multilayer adsorption. The column adsorption study was also evaluated by breakthrough and Thomas models. The Thomas model rate constant kTH (cm3 mg-1 min-1) and maximum solid phase concentration was found to be qo = 2.702 mg·g-1. The thermodynamic study reveals that the adsorption process is exothermic and spontaneous in nature. The kinetic study suggests that the adsorption process follows the pseudo-second-order kinetic model.
- Junejo, Ranjhan,Memon, Shahabuddin,Memon, Fakhar N.,Memon, Ayaz Ali,Durmaz, Fatih,Bhatti, Asif Ali,Bhatti, Ashfaque Ali
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- Oxidative Cyclization of Calixarene
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p-tert-Butylcalixarene was converted in a single step into a system containing carbonyl and ether binding groups.
- Litwak, Ariel M.,Biali, Silvio E.
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- Surface-enhanced micro-raman detection and characterization of calix[4]arene-polycyclic aromatic hydrocarbon host-guest complexes
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Surface-enhanced micro-Raman spectroscopy (micro-SERS) was used to detect traces of the hazardous pollutant polycyclic aromatic hydrocarbons (PAHs) pyrene and benzo[c]phenanthrene deposited onto a calix[4]arene-functionalized Ag colloidal surface. High spectral reproducibility and very low molecular detection limits (10 8 M) were obtained by using 25,27-carboethoxy-26,28- hidroxy-p-tertbutylcalix[4]arene as host molecule. Films of immobilized aggregated Ag nanoparticles, obtained by chemical reduction with hydroxylamine, were prepared by direct adhesion on a glass surface. The influence of the aggregation degree of the initial Ag nanoparticles on the micro-SERS detection effectiveness was checked. Different relative concentrations of the host (calixarene receptor) and the guest (PAHs) were attempted in order to optimize detection of the pollutant. The obtained results indicated that the detection limit is much lower in the case of benzo[c]phenanthrene than in pyrene when exciting with the 785 nm line of a diode laser. A detailed interpretation of the Raman spectra was accomplished in order to obtain more information about the interaction mechanism of the host-guest complex, which could be useful in the future for the design of powerful-detection systems.
- Leyton,Sanchez-Cortes,Campos-Vallette,Domingo,Garcia-Ramos,Saitz
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- Synthesis and properties of novel magnetic nanoparticles grafted with nitropyridine-substituted calix[4]arene derivative as CR6+ extractant
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A new calix[4]arene derivative, 3, which functionalized at the lower rim with 2-(2-aminoethyl amino)-5-nitropyridine, was synthesized and characterized by a combination of FTIR, 1 H NMR, 13 C NMR, and elemental analysis. Then the calix[4]arene 3 was grafted onto [3-(2,3-epoxypropoxy)propyl]trimethoxysilane-modified Fe 3 O 4- nanoparticles (EPPTMS-MN) to produce new calixarene-adorned magnetic nanoparticles (MN-DiNoPy-Calix (4)). The structure of the calixarene-adorned magnetic nanoparticles 4 was determined by a combination of FTIR, TEM, and elemental analysis. Moreover, a study regarding the removal of toxic HCr 2 O-7 anion from aqueous solution was also carried out with the calixarene-adorned magnetic nanoparticles in solid-liquid extraction studies.
- Sayin, Serkan,Dgan, Vildan
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- Synthesis and complexation properties of N,N'-bis(calix[4]arenoxyacetyl) hydrazine derivative
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Heating of p-tert-butylcalix[4]arene bearing acethydrazide moiety at the lower rim in MeCN or PriOH (EtOH) affords the corresponding N,N'-bis(calix[4]arenoxyacetyl)hydrazine derivative. The hydrazinolysis of mono(methoxycarbonylmethoxy)-p-tert-
- Alekseeva, Elena A.,Luk'Yanenko, Aleksandr P.,Gren, Andrei I.
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- Calix[4]arene-based supramolecular gels with unprecedented rheological properties
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A novel calix[4]arene-based dimeric-cholesteryl derivative was synthesized, and its gelation behaviour in thirty organic solvents was investigated. It has been shown that the compound cannot gel any of the pure solvents tested. However, it gels a mixture of solvents n-decane and acetonitrile efficiently, provided the volume ratio of the two solvents in a mixture is within 9:1 and 3:2. AFM and SEM measurements revealed that the molecules of the compound aggregate into micro-/nano-rods first, then fine fibers, and then thick fibers, and finally networked structures in the mixture solvents. Interestingly, the gel with a composition of 1 to 1 (Vn-Decane:VAcetonitrile) and 2.5% (w/v) of the compound exhibits super-smart and fully reversible thixotropic properties, a phenomenon never reported before. Furthermore, the mechanical strength of the gel could be easily adjusted by altering the concentration of the gelator and the composition of the mixture solvents. Further interrogation of the gel revealed that structurally the gel is a gel-emulsion with acetonitrile dispersed in n-decane, a rarely found O/O (oil in oil) gel-emulsion which may find uses in the templated preparation of low-density materials with complicated internal structures.
- Cai, Xiuqin,Liu, Kaiqiang,Yan, Junlin,Zhang, Helan,Hou, Xiaoyu,Liu, Zhang,Fang, Yu
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- "Janus" Calixarenes: Double-Sided Molecular Linkers for Facile, Multianchor Point, Multifunctional, Surface Modification
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We herein report the synthesis of novel "Janus" calix[4]arenes bearing four "molecular tethering" functional groups on either the upper or lower rims of the calixarene. These enable facile multipoint covalent attachment to electrode surfaces with monolayer coverage. The other rim of the calixarenes bear either four azide or four ethynyl functional groups, which are easily modified by the copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC), either pre- or postsurface modification, enabling these conical, nanocavity reactor sites to be decorated with a wide range of substrates to impart desired chemical properties. Redox active species decorating the peripheral rim are shown to be electrically connected by the calixarene to the electrode surface in either "up" or "down" orientations of the calixarene.
- Buttress, James P.,Day, David P.,Courtney, James M.,Lawrence, Elliot J.,Hughes, David L.,Blagg, Robin J.,Crossley, Alison,Matthews, Susan E.,Redshaw, Carl,Bulman Page, Philip C.,Wildgoose, Gregory G.
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- Analytical evaluation of Cu2+ selective behavior of calix[4]arene derivative
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The present article describes the solvatochromic effect including solvent system selection, time study and a detailed complexation study along with exploration of extraction properties of 5,11,17,23-tetrakis[(diethylamino) methyl]-25,26,27,28-tetrahydroxycalix[4]arene (4) that bears nitrogen atom as a donor group available for chelating metal ions. Complexation properties of 4 toward selected transition metal ions have been investigated by UV-visible and fluorescence spectroscopies. The% efficiency of 4 toward selected transition metal ions was found in order Cu2+> Ni2+> Hg 2+> Zn2+> Co2+> Cd2+> Pb2+. It has been noticed that 4 is not only proved to be an efficient Cu2+ selective chromoionophore but also possesses an effective extraction property for transferring Cu2+ ions from an aqueous to dichloromethane layer. The FT-IR spectroscopic method has also been applied for further confirmation of the complexation phenomenon of 4 with Cu2+ ion and found adequate. Springer Science+Business Media, LLC 2009.
- Qazi, Mansoor Ahmed,Qureshi, Imdadullah,Memon, Shahabuddin
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- Synthesis and characterization of novel nanofiber based calixarene and its binding efficiency towards chromium and uranium ions
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The objective of this study is to obtain nanofibrous precursor based calixarene with high ion adsorption capacity by electrospinning of blended solution of polyacrylonitrile (PAN) and upper rim functionalized calix[4]arene bearing N-methylglucamine (Calix-NMG). The obtained electrospun fibers were characterized using fourier transform infrared (FT-IR-ATR), scanning electron microscope (SEM) equipped with energy-dispersive X-ray spectrometry (EDX) and thermogravimetric analyses (TGA and DSC). Analysis indicated that preparation of nanofibers based Calix-NMG was successfully achieved. The ion binding studies exhibited that the nanofiber based Calix-NMG could be efficiently used for the binding of chromate anions and uranium cations. Nanofiber based calix[4]arene with N-methylglucamine chelating groups may be a good candidate as a filter material for treatment of a large quantity of wastewater owing to their very large surface area as well as both the inclusion and donor–acceptor complexation capability of all surfaces associated with the calixarene skeleton.
- ?zcan, Fatih,Bayrakc?, Mevlüt,Ertul, ?eref
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- Easy and selective method for the synthesis of various mono-O- functionalized Calix[4]arenes: De-O-functionalization using TiCl4
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An efficient and selective method for the monofunctionalization of p-tert-butylcalix[4]arene is described. A mono-de-O-functionalization of disubstituted p-tert-butylcalix[4]arenes using titanium tetrachloride was developed to synthesize a series of monosubstituted p-tert-butylcalix[4]arenes with the pendant functions being ethoxycarbonylmethyloxy, 3- ethoxycarbonylpropyloxy, cyanomethyloxy, 3-cyanopropyloxy, 4-bromobutyloxy, 3-hydroxypropyloxy, propyloxy, 2-methylpropyloxy, 3-butynyloxy, and 3-cyanopropyloxy groups. The reaction mechanism of the formation of 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-ethoxycarbonylpropyloxy) calix[4]arene was studied by 1H NMR and GC/mass spectroscopy monitoring. Reaction of TiCl4 with the disubstituted p-tert-butylcalix[4]arene produced the corresponding dioxocalix[4]arene titanium dichloride complex, which undergoes elimination of ethyl 4-chlorobutyrate, leading to a trioxocalix[4]arene titanium dichloride complex and to monosubstituted calix[4]arene after hydrolysis. These two complexes were also synthesized, isolated, and fully characterized.
- Bois, Joackim,Espinas, Jeff,Darbost, Ulrich,Felix, Caroline,Duchamp, Christian,Bouchu, Denis,Taoufik, Mostafa,Bonnamour, Isabelle
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- Scaling up the Synthesis of a Hydroxyquinoline-Functionalized p-tert-Butylcalix[4]arene
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The optimization for an upscaled technical production of a lower rim-functionalized p-tert-butylcalix[4]arene, furnished with N4O4-donor ligands for superior solvent extraction separation between heavy and light lanthanides, is described. We demonstrate that reducing the polarity of the aprotic solvent in the (1,3)-distal esterification of p-tert-butylcalix[4]arene 1 does not compromise the quality or yield of product 2. It was possible to use the technical quality educt 1, that is, without prior crystallization in toluene, in conjunction with reductions in reaction time and solvent volume. The raw diester product 2 could be used, without prior recrystallization (which originally required 3 days) in the condensation reaction with hydrazine monohydrate to form hydrazide 3. Most importantly, the solvent volume required in the final condensation reaction of 3 with 8-hydroxyquinoline-2-carboxaldehyde could be reduced by an order of magnitude by using chloroform. Not only was the final disubstituted product yield improved but also the purity of the final product could be ensured by preventing the precipitation of the intermediate monosubstituted product during reaction. The filtration characteristics of the final product, as well as its solvation properties during solvent extraction of lanthanides were significantly improved.
- Roode-Gutzmer, Quirina I.,Holderied, Lara N.,Glasneck, Florian,Kersting, Berthold,Fr?hlich, Peter,Bertau, Martin
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- Synthesis and DFT calculation of a novel 5,17-di(2-antracenylazo)-25,27-di(ethoxycarbonylmethoxy)-26,28-dihydroxycalix[4]arene
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In this study, 5,17-di(2-antracenylazo)-25,27-di(ethoxycarbonylmethoxy)-26,28-dihydroxycalix[4]arene has been synthesized from 2-aminoantracene and 25,27-dihydroxy-26,28-diethylacetate calix[4]arene. In order to identify the molecular structure and vibrational features of the prepared azocalix[4]arene, FT-IR and 1H NMR spectral data have been used. FT-IR spectrum of the studied molecule is recorded in the region 4000-400 cm-1. 1H NMR spectrum is recorded for 0.1-0.2 M solutions in DMSO-d6 solution. The molecular geometry, infrared spectrum are calculated by the density functional method employing B3LYP level with different basis sets, including 6-31G(d) and LanL2DZ. The chemical shifts calculation for 1H NMR of the title molecule is calculated by using by Gauge-Invariant Atomic Orbital method by utilizing the same basis sets. The total density of state, the partial density of state and the overlap population density of state diagram analysis are done via GaussSum 3.0 program. Frontier molecular orbital (HOMO-LUMO) and molecular electrostatic potential surface on the title molecule are carried out for various intramolecular interactions that are responsible for the stabilization of the molecule. The experimental results and theoretical calculations have been compared, and they are found to be in good agreement.
- Bayrakdar,Kart,Elcin,Deligoz,Karabacak
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- Synthesis of the porphyrin-calix[4]arene conjugates via Pd-catalyzed amination and their evaluation as fluorescent chemosensors
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The synthesis of the porphyrin-calix[4]arene conjugates was carried out using the Pd(0)-catalyzed amination of Zn(II) meso-(3-bromophenyl)porphyrinate with bis(3-aminopropoxy)substituted calix[4]arenes (in cone and 1,3-alternate conformations). One of the conjugates was demetalated to give free porphyrin base derivative. The investigation of the fluorescence of the conjugates was studied in the presence of 18 metal perchlorates. The zinc porphyrinate derivatives were found to quench fluorescence in the presence of Cu(II), Al(III) and Cr(III) cations as well as on protonation. Metal-free conjugate was shown to act as a molecular probe for Zn(II), Cu(II) and Cd(II) cations due to strong and different changes of the emission caused by these metals.
- Yakushev, Alexei A.,Averin, Alexei D.,Sakovich, Maria V.,Vatsouro, Ivan M.,Kovalev, Vladimir V.,Syrbu, Sergei A.,Koifman, Oskar I.,Beletskaya, Irina P.
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- The synthesis of new calix[n]arene quaternary ammonium salts and investigation of their catalytic affinities for three component Mannich-type reactions in water
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Two new calix[n]arenes and a non-cyclic analogue substituted with 1-(2-furoyl)piperazine have been synthesized. Moreover, their quaternary ammonium salts have been prepared by treatment with methyl iodide. All of the new quaternary ammonium salts have been employed as catalysts in one-pot Mannich reactions to afford β-aminocarbonyl compounds. The combination of good to excellent yields, the need for a small amount of catalyst and simple work-up, mean that this route can be considered to be green chemistry.
- Sayin, Serkan,Yilmaz, Mustafa
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- Synthesis of new anthracene-substituted calix[4]triazacrown-5 as highly sensitive fluorescent chemosensor and extractant against hazardous dichromate anion
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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.
- Sayin, Serkan
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- Convenient one pot procedure for synthesis of formylated calix[n]arenes
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A convenient one pot procedure for obtaining formyl calix [n]arenes via condensation with 1,1-dichloromethylmethylether is described.
- Chawla,Santra
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- Enzyme-responsive supramolecular nanovalves crafted by mesoporous silica nanoparticles and choline-sulfonatocalix[4]arene [2]pseudorotaxanes for controlled cargo release
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Mesoporous silica nanoparticles (MSNs) have been surface-functionalized with choline moieties encircled by sulfonatocalix[4]arenes. Two enzyme cleavable sites are incorporated in the stalks for specific enzymes to regulate the release of loaded cargos from MSNs. These gated materials show a clear enzymatic response and proven orthogonality.
- Sun, Yu-Long,Zhou, Yue,Li, Qing-Lan,Yang, Ying-Wei
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- An Elaborate Supramolecular Assembly for a Smart Nanodevice for Ratiometric Molecular Recognition and Logic Gates
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Ingenious approaches to supramolecular assembly for fabricating smart nanodevices is one of the more significant topics in nanomaterials research. Herein, by using surface quaternized cationic carbon dots (CDots) as the assembly and fluorescence platform, anionic sulfonatocalix[4]arene with modifiable lower and upper rims as a connector, as well as in situ coordination of Tb3+ions, we propose an elaborate supramolecular assembly strategy for the facile fabrication of a multifunctional nanodevice. The dynamic equilibrium characteristics of the supramolecular interaction can eventually endow this nanodevice with functions of fluorescent ratiometric molecular recognition and as a nano-logic gate with two output channels. A smart nanodevice for ratiometric molecular recognition and nano-logic gates has been successfully fabricated by using an elaborate supramolecular assembly strategy that includes the precise assembly of a bifunctional connector sulfonatocalix[4]arene on quaternized cationic carbon dots by inclusion complexation and electrostatic interactions, and the incorporation of Tb3+ions by in situ coordination.
- Xie, Yu-Jie,Wu, Wen-Yu,Chen, Hao,Li, Xiang,Zhang, Hao-Li,Liu, Liang-Liang,Shao, Xing-Xin,Shan, Chang-Fu,Liu, Wei-Sheng,Tang, Yu
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- Absorption of chlorinated hydrocarbons dissolved in water with pellets made of p-tert-butylcalix[4]arene and silica gel
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Powdery crystals of p-tert-butylcalix[4]arene (1) pelletized using silica gel as a binder absorb chlorinated hydrocarbons from saturated aqueous solutions by forming inclusion complexes with compound 1.
- Morohashi, Naoya,Shibata, Ozora,Hattori, Tetsutaro
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- Calix[4]arene based highly efficient fluorescent sensor for Au3+ and I-
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This approach disclose the selective fluorogenic ion sensing ability of 5,11,17,23-tetratertbutyl-25,27-bis((2hydroxynaphthylimino)1,2-ethylenediaminecarbonylmethoxy)-26,28 dihydroxycalix[4]arene (C4NSB). Binding property of receptor probed by using selected various cations and anions with conferring of results that demonstrates 'turn-off' fluorescence response and significantly high chromogenic selectivity toward Au3+ and I-. Furthermore, selective nature of receptor was investigated in the presence of different co-existing competing ions. The limit of detection (LOD) for Au3+ and I- was determined as 1.5∈×∈10-5 and 4.5∈×∈10-6 M respectively. Receptor C4NSB form (1:1) stoichiometric complex with both ions and their binding constants were calculated as 8.0∈×∈102 for Au3+ and 15.6∈×∈102 M-1 for I-. Complexes were also characterized through FT-IR spectroscopy.
- Memon, Shahabuddin,Bhatti, Ashfaque Ali,Bhatti, Asif Ali,Ocak, ümmühan,Ocak, Mira?
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- Two coordination polymers based on p-tert-butylcalix[4]arene as efficient luminescent sensor for Fe3+ and MnO4? ions
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We herein report two coordination polymers [Cd2L(H2O)4]·CH3OH·DMF (1) and [Mn2L(H2O)3(CH3O)]·(NH2CH3)2·3CH3OH·H2O (2) assembled with a novel p-tertbutylcalix[4]arene ligand (H4L = tetrakis [(2-biphenylcarboxyl)oxy]-p-tertbutylcalix[4]arene). Isostructural coordination polymers 1 and 2 feature layer structures, which are further linked by hydrogen bonds to generate supramolecular double layers. The luminescent character of 1 in different ions and anions were explored. The quenching to Fe3+ and MnO4? in water makes 1 into a promising luminescent sensor.
- Liu, Ying-Ying,Ma, Jian-Fang,Sun, Ze-Chen
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- Extraannular fluorinated calixarenes: Regiospecificity of the deoxofluorination reactions of bis(spirodienol) derivatives
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A new route for the partial displacement of OH groups of p-tert-butylcalixarene via spirodienol derivatives is described. NaBH4 reduction of the bis(spirodienone) calixarene derivatives 2a-2c afforded the corresponding bis(spirodienols) 3a-3c in stereospecific fashion. 1H NMR NOESY spectroscopy indicated that in the case of 2a, the reaction proceeds by attack at the exo face of the two carbonyls (the face located anti to the spiro C-O bond). The spirodienols readily revert to p-tert-butylcalix[4]arene when heated. The reaction of 3a with the deoxofluorinating agent DAST (Et2NSF3) afforded a mixture of extraannular substituted calixarenes possessing one or two fluoro-substituted dehydroxylated rings. The bisfluorinated calixarene 6a adopts in the crystal a conformation (1,3-alternate) similar to that adopted in solution by the di-dehydroxylated calixarene 6b. An experiment conducted with a selectively deuterated spirodienol derivative indicated that the deoxofluorination reaction involves regiospecific nucleophilic attack at the γ position of the pentadienol subunit.
- Agbaria,Woehnert,Biali
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- Bifunctional Calix[4]arene Sensor for Pb(II) and Cr2O 7 2- Ions
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A readily available chromionophore 5,11,17,23-tetra-tert-butyl-25,27- bis(hydrazidecarbonylmethoxy)-26,28-dihydroxycalix[4]arene (HCC4) was employed as a chromogenic sensing probe selective for Pb(II) and Cr2O 7 2- ions among a series of various ions such as Li(I), Na(I), K(I), Rb(I), Ba(II), Sr(II), Al(III), Cd(II), Co(II), Cu(II), Hg(II), Ni(II), Pb(II) and Zn(II) as well as Cr2O7 2-, CH3CO2 -, Br-, Cl-, F-, I-, ClO4 - and NO3 - that have been examined by UV-visible and fluorescence spectroscopic techniques. The HCC4 in DCM-MeCN system forms 2:1 (ligand-metal) complex with Pb(II). It also shows 2:1 stoichiometry with Cr2O 7 2-. The complexation phenomenon has been confirmed by FTIR spectroscopy that favors the selective nature of HCC4 with Pb(II) and Cr2O7 2-. Thermal gravimetric analysis (TGA) also supports its utility in drastic conditions.
- Qazi, Mansoor Ahmed,Ocak, ümmühan,Ocak, Mira?,Memon, Shahabuddin,Solangi, Imam Bakhsh
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- A novel calix[4]arene-based dimeric-cholesteryl derivative: Synthesis, gelation and unusual properties
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A calix[4]arene-based dimeric-cholesteryl derivative with naphthalene in the linkers (C2N2C) was designed and synthesized. The gelation behaviors of the compound in 36 liquids were evaluated. It was demonstrated that C2N2C could gel 16 of the liquids tested, which include both polar and apolar liquids. SEM and AFM studies revealed that the morphologies of the gel networks are dependent on the concentrations of C2N2C and the nature of the liquids under study. Importantly, rheological studies revealed that the gel of the compound in benzene possesses sensitive, fast and fully reversible thixotropic property. More importantly, the Tgel of the C2N2C/benzene gel could be at least more than 60 degrees higher than the boiling point of benzene when the gelator concentration is greater than 6% (w/v), a result never reported before. CD measurements revealed the chiral nature of the assemblies of the gel networks. Further investigation by AFM measurements confirmed the right-hand helical structures of the gel networks of C2N2C/benzene gel. As anticipated, hydrogen bonding and π-π stacking are the two main driving forces for the formation of the gels.
- Wu, Ying,Liu, Kaiqiang,Chen, Xiangli,Chen, Yongping,Zhang, Shaofei,Peng, Junxia,Fang, Yu
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- Adsorption of phenolic compounds onto calix[4]arene-bonded silica gels from aqueous solutions
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This article describes the preparation of calix[4]arene-bonded silica gels (C[4]BS and DMC[4]BS), and their application to the removal of some selected phenolic compounds such as phenol (PHE), p-chlorophenol (PCP), m-nitrophenol (MNP) and p-nitrophenol (PNP) from aqueous solutions by adsorption method. In initial adsorption experiments appeared that C[4]BS was much more effective in adsorption of PNP rather than PHE, PCP and MNP, whereas DMC[4]BS exhibited too little adsorption ability towards all phenols. Herein, it was concluded that the hydrogen bonding capacities of both phenols and calix[4]arene based adsorbents played a predominant role in the interactions between adsorbate and adsorbent within the adsorption mechanism. Thus, in subsequent studies, the C[4]BS was employed as an adsorbent in the adsorption of PNP, and adsorption conditions were optimized. Furthermore, isotherm and kinetic studies were performed to clarify the phenomena of PNP adsorption onto C[4]BS.
- Dolaksiz, Yasemin Ekin,Temel, Farabi,Tabakci, Mustafa
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- Reversible coloring/decoloring reactions of thermochromic leuco dyes controlled by a macrocyclic compound developer
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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.
- Chaodongbung, Tawatchai,Kaewtong, Chatthai,Pattavarakorn, Datchanee,Saenkham, Audchara,Sriphalang, Sanguansak,Wanno, Banchob
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- Synthesis of new anthracene-conjugated calix[4]arene as highly selective fluorescent chemosensor for determination of CN? ion
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A new calix[4]arene derivative substituted with anthracene at its 1,3-distal position was synthesized via a simple Schiff base reaction, and its structure was fully characterized by using ATR-FTIR, 1H-NMR, 13C-NMR, ESI-MS and elemental analysis techniques. Furthermore, the ion binding feature of the anthracene substituted calix[4]arene (Ant-Calix) was evaluated against Br?, Cl?, F?, HSO4?, NO3? and CN? ions. Various aspects of anion sensing phenomena were deeply assessed, and the findings addressed that Ant-Calix exhibited excellent selectivity for CN? and could detect in a very low detection limit 92.4 nM. Beside, when CN? ion was bound to the probe Ant-Calix, a significant color change from light green to pink color was observed under UV light. The fluorescence data was also employed to calculate the binding stoichiometry and association constant of the complex obtained between Ant-Calix and cyanide ion. In addition, the 1H-NMR technique was also used to elucidate the mechanism of the complex formation between Ant-Calix and CN?.
- Sayin, Serkan
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- Inclusion complexes of water-soluble calix[n]arenes with quercetin: preparation, characterization, water solubility, and antioxidant features
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This study focuses on the construction of two new inclusion complexes of quercetin with p-sulfonatocalix[4]arene-tetracarboxylic acid and/or p-sulfonatocalix[8]arene-octacarboxylic acid, so that the drug gets soluble in an aqueous media. The structures of
- Ozyilmaz, Elif,Arpaci, Pembegul Uyar,Sayin, Serkan,Yildirim, Ayse,Ascioglu, Sebahat,Gok, Emine
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p. 201 - 209
(2022/01/20)
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- Optimization of toxic metal adsorption on DEA-calix[4]arene appended silica resin using a central composite design
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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.
- Gul, Samiha,Memon, Fakhar N.,Memon, Shahabuddin
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p. 3448 - 3463
(2022/02/21)
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- Mathematical modeling studies for the adsorptive removal of ciprofloxacin drug from water samples using functionalized silica resin
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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.]
- Elik, Mustafa,Jalbani, Nida Shams,Junejo, Ranjhan,Kaya, Savas,Serdaroglu, Goncagül
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- Viologen-cucurbituril host/guest chemistry - redox control of dimerizationversusinclusion
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Two calix[4]arene systems,C234+andC244+- where 2 corresponds to the number of viologen units and 3-4 corresponds to the number of carbon atoms connecting the viologen units to the macrocyclic core - have been synthesized and led to t
- Dalvand, Parastoo,Nchimi Nono, Katia,Shetty, Dinesh,Benyettou, Farah,Asfari, Zouhair,Platas-Iglesias, Carlos,Olson, Mark A.,Trabolsi, Ali,Elhabiri, Mourad
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p. 29543 - 29554
(2021/10/08)
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- Columnar self-assembly, electrochemical and luminescence properties of basket-shaped liquid crystalline derivatives of Schiff-base-moulded: P-tert -butyl-calix[4]arene
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A new family of supramolecular liquid crystalline compounds with a calix[4]arene core and two linking groups appended on four sides, exhibiting a wide range of hexagonal columnar phases, has been synthesised and well characterised. The liquid crystal beha
- Sharma, Vinay S.,Sharma, Anuj S.,Worthington, Sheena J. B.,Shah, Priyanka A.,Shrivastav, Pranav S.
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supporting information
p. 20610 - 20619
(2020/12/28)
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- Turn on fluorescence strip based sensor for recognition of Sr2+ and CN? via lowerrim substituted calix[4]arene and its computational investigation
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Fluorescence sensor L designed around a calix[4]arene scaffold, bearing two fluorogenic aminoquinoline moities, has been synthesized. It is found to be selective and sensitive towards Sr2+ and CN? over a wide range of cations and anions in a spectrofluorometric study in acetonitrile. The ion-binding property of L was monitored by fluorescence spectroscopy, UV–vis spectroscopy, ESI-MS, 1H NMR, FT-IR investigation and PXRD study. The host L shows a minimum detection limit which is 1.36 nM for Sr2+ and 1.23 nM for CN? having concentration range 5–120 nM and 5–115 nM respectively. The calculated binding constants for L:Sr2+ and L: CN? are respectively 8.859 × 108 M?1 and 8.574 × 108 M?1. Our host L has been utilised in formation of a user-friendly, affordable, and disposable paper-based analytical device (PAD) for rapid chemical screening of Sr2+ and CN? ion via single strip. Moreover, the optimization of probe L has also been done by the MOPAC-2016 software package using NM7 popular method resulting ?21.71 kcals/mol heat of formation and also determined the HOMO-LUMO energy band gap for L, L:Sr2+ and L: CN?. Further, molecular docking score has been calculated using HEX software. The applicability of our probe in real samples containing Sr2+ and CN? has also been checked by emission study with 94–99% recovery.
- Sutariya, Pinkesh G.,Soni, Heni,Gandhi, Sahaj A.,Pandya, Alok
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supporting information
(2020/05/18)
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- CALIXCROWNS AND USES THEREOF
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Provided herein are novel calixcrowns, such as those of Formula (I), which are useful for coating a solid substrate such as a protein chip, diagnostic kit or protein separation pack. Also provided herein are methods detecting protein-protein interactions with a solid substrate coated with the calixcrown herein and an immobilized protein.
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Paragraph 0060
(2020/10/09)
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- Improvement of the anticancer activity of chlorambucil and ibuprofen via calix[4]arene conjugates
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Background: One of the possible ways of improving the activity and selectivity profile of anticancer agents is to design drug carrier systems employing nanomolecules. Calix[4]arene derivatives and chlorambucil and ibuprofen are important compounds that ex
- Organista-Mateos, Ulises,Allende-Alarcón, Luis Isaac,Martínez-García, Marcos,Martínez-Klimova, Elena,Pedro-Hernández, Luis D.,Ramírez-ápan, Teresa
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p. 984 - 990
(2020/08/19)
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- MOLECULES THAT STIMULATE THE IMMUNE SYSTEM FOR TREATMENT OF DRUG ADDICTION, METHODS OF SYNTHESIS, ANTIDRUG VACCINE AND USES
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This technology relates to immune system stimulating molecules to be used in the treatment of drug addiction and abuse and their synthesis processes. These molecules have a calixarene chemical structure, preferably calix[4]arene and/or calix[8]arene, coupled to an hapten analogous to cocaine, preferably GNE and/or GNC. An anti-drug vaccine, specifically anti-cocaine, is also described using such molecules. The anti-drug vaccine can be also used to prevent fetal exposure to drugs in pregnant women who use drugs and do not wish or cannot stop their use during pregnancy.
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Paragraph 0020; 0143; 0145-0148
(2020/12/20)
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- Calixarenes functionalised water-soluble iron oxide magnetite nanoparticles for enzyme immobilisation
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In this study, we first used water-soluble iron oxide nanoparticles for Candida rugosa lipase immobilisation. Moreover, two new complexation phenomena of the prepared water-soluble Fe3O4 nanoparticles with an enzyme might address int
- Sayin, Serkan,Ozyilmaz, Elif,Oguz, Mehmet,Yusufoglu, Rüstem,Yilmaz, Mustafa
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p. 334 - 344
(2020/03/30)
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- Investigation of high-performance adsorption for benzene and toluene vapors by calix[4]arene based organosilica (CBOS)
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The immobilization of a calix[4]arene derivative bearing methyl ester moieties onto mesoporous silica was successfully achieved to obtain calix[4]arene based organosilica (CBOS). IR spectroscopy, X-Ray powder diffraction, energy-dispersive spectroscopy, and scanning electron microscopy analysis were carried out for the characterization of the CBOS. After that, the proposed mesoporous silica-supported adsorbent was studied for the adsorption of benzene and toluene vapors, which are essential VOCs. The effects of operating parameters on the adsorption of these vapors with the CBOS adsorbent were analyzed and optimized by applying response surface methodology (RSM)-central composite design (CCD). According to initial experimental results, CBOS exhibited excellent performance for these vapors. The adsorption capacities of calix-3, GBS, and CBOS adsorbents were determined to be 203, 357, and 606 mg g-1 for benzene vapors, respectively, while they were found to be 258, 394 and 672 mg g-1 for toluene vapors, respectively. Thus, the proposed CBOS adsorbent showed better adsorption performance when compared to its precursors. In addition to the distinctive adsorptive behavior, the CBOS adsorbent exhibited a high reproducibility adsorption/desorption capacity after five consecutive cycles. After the fifth adsorption/desorption cycle, the CBOS retained 94.2% and 95.1% of its initial adsorption capacities for benzene and toluene, respectively. Finally, adsorption phenomena of benzene and toluene vapors onto CBOS were evaluated in terms of isotherm and kinetic parameters. This journal is
- Temel, Farabi,Kutluay, Sinan
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p. 12949 - 12961
(2020/08/28)
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- Synthesis of Core-Shell Magnetic Supramolecular Nanocatalysts based on Amino-Functionalized Calix[4]arenes for the Synthesis of 4H-Chromenes by Ultrasonic Waves
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One of the most common phenol-formaldehyde cyclic oligomers from hydroxyalkylation reactions that exhibit supramolecular chemistry are calixarenes. These macrocyclic compounds are qualified to act as synthetic catalysts due to their specific features incl
- Eivazzadeh-Keihan, Reza,Noruzi, Ehsan Bahojb,Radinekiyan, Fateme,Salimi Bani, Milad,Maleki, Ali,Shaabani, Behrouz,Haghpanahi, Mohammad
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p. 735 - 742
(2020/04/22)
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- Path to Industrial Production of Calix[8 and 4]arenes
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A highly selective and high yield synthesis for the production of calix[8]arenes in concentrated reaction masses is described. Obtained purities are >98% and yields of >80%, with isolation by simple filtration. The developed approach allows for subsequent
- Haase, Cornelius Heinz Werner
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p. 603 - 611
(2020/02/04)
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- Luminescent behavior of pyrene-allied calix[4]arene for the highly pH-selective recognition and determination of Zn2+, Hg2+ and I-: Via the CHEF-PET mechanism: Computational experiment and paper-based device
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In this article, for the first time, we have reported a novel CHEF-PET fluorescence sensor L based on calix[4]arene containing four pyrene groups as binding sites, which is highly selective and sensitive towards Zn2+, Hg2+ and I-. This fluorescence probe was synthesized and characterized using the emission study, UV-vis titration, 1H NMR spectroscopy and ESI-MS investigation. The linear concentration range at pH 7 of L for Zn2+, Hg2+ and I- is 0-135 nM, 0-140 nM and 0-120 nM, respectively, with the detection limit of 6.43 nM for Zn2+, 2.94 nM for Hg2+ and 20.93 nM for I-. The binding ability was determined through Benesi-Hildebrand equation, which was found to be 7.535 × 108 M-1 for Zn2+, 9.001 × 108 M-1 for Hg2+ and 8.139 × 108 M-1 for I-. Further, we reported an easy-to-use, low-cost and disposable paper-based sensing device for the rapid chemical screening of Zn2+, Hg2+ and I-. The device comprises luminescent sensing probes embedded into a cellulose matrix, where the resonance energy transfer phenomenon seems to be the sensing mechanism. It opens up new opportunities for simple and fast screening in remote settings, where sophisticated instrumentation is not always available. The MOPAC-2016 software package was used to optimize the L using the well-established PM7 method and calculate the HOMO-LUMO energy band gap for structure L and L with Zn2+, Hg2+ and I- ion-based structures. The molecular docking study was carried out using HEX software.
- Sutariya, Pinkesh G.,Soni, Heni,Gandhi, Sahaj A.,Pandya, Alok
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supporting information
p. 9855 - 9864
(2019/07/04)
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- Bowl-shaped fluorescent liquid crystals derived from 4-: Tert butyl calix[4]arene and trans cinnamic acid derivatives
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A new family of bowl-shaped molecules with a calix[4]arene rigid core appended by four-side and two-side substitution with trans 4-n-alkoxy cinnamic acid has been synthesized and well characterized. The LC behaviours of the novel materials were studied by using optical polarising microscopy, differential scanning calorimetry and high-temperature powder X-ray diffraction methods to confirm the smectic organization. It is found that all of the prepared materials display enantiotropic LC phases in the present series-1 (1d4-1, 1d5-l, 1d8-1, 1d10-l, 1d12-l, 1d14-l) and series-2 (1d4-1l, 1d5-ll, 1d8-1l, 1d10-ll, 1d12-ll, 1d14-ll). The electrochemical behaviour shows the higher reactivity of the proposed derivatives, which is in good agreement with the DFT values. The relationship between the structure and the mesomorphic behaviour of the compounds in both series is discussed. These synthesized supramolecular compounds show blue luminescence in solution as well as in solid thin films under long wavelength UV light. To get more insights, HOMO and LUMO studies were carried out, which support intramolecular charge transfer interactions in this class of mesogens.
- Sharma, Vinay S.,Singh, Hemant Kumar,Sharma, Anuj S.,Shah, Akshara P.,Shah, Priyanka A.
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p. 15575 - 15584
(2019/10/19)
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- Calix[4]arene-based polyoxometalate organic-inorganic hybrid and coordination polymer as heterogeneous catalysts for azide-alkyne cycloaddition and Knoevenagel condensation reaction
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Based on a neutral pyridyl-functional calix[4]arene ligand (L = tetrakis [(3-pyridylmethyl)oxy]-p-tertbutylcalix[4]arene), one polyoxometalate-based organic-inorganic hybrid [Cu2L(SiW12O40)0.5]·CH3CN·
- Yue, Liu-Juan,Liu, Ying-Ying,Xu, Guo-Hai,Ma, Jian-Fang
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supporting information
p. 15871 - 15878
(2019/10/22)
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- Water-soluble nitrogen-containing calixarene
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The invention relates to a water-soluble nitrogen-containing calixarene. The preparation method comprises: carrying out a dealkylation reaction on p-tert-butylcalix[4]arene as a raw material and phenol in the presence of anhydrous aluminum trichloride to
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Paragraph 0014-0015
(2019/05/16)
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- Method for preparing high-purity resveratrol
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The invention relates to a method for preparing high-purity resveratrol. The method comprises the following steps: synthesizing calixarene RS002 with capability of identifying 3,4'-dihydroxystilbene through aldol condensation, Friedel-Crafts reaction, est
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Paragraph 0022; 0023
(2019/04/13)
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- Water-soluble nitrogen-containing calixarene synthesis method
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The invention relates to a water-soluble nitrogen-containing calixarene synthesis method, which comprises: carrying out a dealkylation reaction on p-tert-butylcalix[4]arene as a raw material and phenol in the presence of anhydrous aluminum trichloride to
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Paragraph 0014-0015
(2019/05/16)
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- Phase transfer catalyst based on calixarene structure, preparation method thereof, and method for producing fluorinated organic compounds using the same
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When using a catalyst represented by chemical formula 1 according to the present invention in manufacturing an organic fluorinated compound by conducting a reaction of alkyl halide or alkyl sulfonate, potassium fluoride or cesium fluoride, which is a fluoride salt, an alkali positive ion is combined with a crown ether group and a fluorine negative ion is hydrogen-bonded with a hydroxy group to weaken ionic bonds of alkali metal fluoride to promote a fluorination reaction, and also to have an effect of significantly inhibiting the production of by-product alkenes.COPYRIGHT KIPO 2020
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Paragraph 0181-0182; 0185-0195
(2019/12/25)
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- Columnar self-assembly of bowl shaped fluorescent liquid crystals based on calix[4]arene with Schiff base units
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A new family of bowl-shaped molecules with a calix[4]arene rigid core and appended on four-sides, that display a wide range of hexagonal columnar phases, has been synthesised and well characterized. The thermal behaviours of the present compounds were established using a combination of polarising optical microscopy (POM), differential scanning calorimetry (DSC) and a high-temperature powder X-ray diffraction method (XRD). It is found that all of the synthesised materials show an enantiotropic hexagonal columnar liquid crystal phase. The structural and conformation characterization of these newly synthesised compounds was achieved by FT-IR, 1H NMR, and 13C NMR spectroscopy. All of the synthesised compounds exhibited good blue luminescence in solution under long wavelength UV light. To explore the structure property correlations, the alkoxy side chain group was varied from a lower alkyl spacer to a higher alkyl spacer on the lower rim of the calix[4]arene. The present research specified that the introduction of linking groups on the lower rim with an n-alkoxy side group is an influential approach to obtaining a supramolecular bowl shape liquid crystal which has good thermal and photophysical behaviour.
- Sharma, Anuj S.,Sharma, Vinay S.,Vekariya, Rajesh H.
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supporting information
p. 15044 - 15051
(2018/09/29)
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- Probe for detecting multi-target alkaline earth metal ions and application thereof
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The invention discloses a probe for detecting multi-target alkaline earth metal ions and application thereof. The probe has unique structural design. The upper side of calixarene is modified by a double bond with nitrogen iodide methyltetramethylpyridine, so as to not only constitute a large conjugated structure, but also improve luminous efficiency. At the same time, quaternary ammonium salt improves the water solubility of the probe. The carboxyl modification of the lower edge of calixarene provides more complexation sites; in addition, the probe can be used for detecting multiple targets independently. Fluorescence quenching and ratio absorption methods are used to selectively detect three alkaline earth metal target ions with high sensitivity and low detection limit. The detection method can be used to carry out both spectral detection and rapid visual colorimetric detection.
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Paragraph 0096; 0099; 0100; 0102; 0103
(2018/10/19)
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- Quinolines: Microwave-assisted synthesis and their antifungal, anticancer and radical scavenger properties
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An efficient method for the synthesis of quinolines using microwave irradiation was developed providing 28 quinolines with good yields. The reaction procedures are environmentally friendly, convenient, mild and of easy work-up. Quinolines were evaluated f
- Liberto, Natália Aparecida,Sim?es, Juliana Baptista,de Paiva Silva, Sarah,da Silva, Cristiane Jovelina,Modolo, Luzia Valentina,de Fátima, ?ngelo,Silva, Luciana Maria,Derita, Marcos,Zacchino, Susana,Zu?iga, Omar Miguel Portilla,Romanelli, Gustavo Pablo,Fernandes, Sergio Antonio
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supporting information
p. 1153 - 1162
(2017/02/05)
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- Preparation of calix[4]arene-embedded polysulphone membranes, and utilisation of its Cr(VI) transport efficiency
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In this study, a tetramine-substituted calix[4]arene derivative, which was synthesised from calix[4]arene by treatment with dimethylamine in one step via Mannich reaction, was used to fabricate a new calix[4]arene-embedded polysulphone membrane (calix@membrane). Its structure and surface morphology were determined using thermogravimetric analysis and scanning electron microscopy, and elemental analysis techniques. Moreover, a Donnan dialysis system was employed to investigate Cr(VI) transport efficacy of calix@membrane at different pH values. Results showed that calix@membrane represented a promising transport capability for HCr2O7 ? due to their efficient complexation behaviour.
- Engin, Mehmet Soner,Cay, Seydahmet,Sayin, Serkan,Eymur, Serkan,Sardohan Koseoglu, Tugba
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p. 455 - 461
(2017/03/24)
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- Design, synthesis and characterization of quinoline-pyrimidine linked calix[4]arene scaffolds as anti-malarial agents
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In this paper, we report a series of quinolinepyrimidine linked calix[4]arene derivatives functionalized with 8-amino quinoline, 5-amino quinoline, 8-hydroxy quinoline, 2-amino pyrimidine and 4-amino 3-methyl quinoline. The synthesized compounds were purified and characterized by elemental analysis, FT-IR,1H NMR and ESI-MS and screened for their anti-malarial activity against plasmodium falciparum strains. Two synthesized compounds with 8-hydroxy quinoline and 2-amino pyrimidine substituents showed good antimalarial activity with IC50 0.073 and 0.043 μg/ml respectively which is comparable with the standard drug chloroquine. The present study provides valuable information for developing calix[4]arene conjugates quinoline-pyrimidine based derivatives as an effective antimalarial agents. Graphical Abstract In this paper, we report a series of quinoline-pyrimidine linked calix [4]arenes derivatives functionalised with 8-amino quinoline, 5-amino quinoline, 8-hydroxy quinoline, 2-amino pyrimidine and 4-amino 3-methyl quinoline and screened for antimalarial activity. Two synthesized compounds with 8-hydroxy quinoline and 2-amino pyrimidine substituents showed good antimalarial activity with IC50 0.073 and 0.043 μg/mL respectively, which is comparable with the standard drug chloroquine. The present study provides valuable information for developing calix[4]arene conjugates quinoline-pyrimidine derivatives.
- Shah, Rahul B.,Valand, Nikunj N.,Sutariya, Pinkesh G.,Menon, Shobhana K.
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p. 173 - 178
(2016/07/29)
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- Synthesis of a series of novel tetra-tert-butylcalix[4]arene linked to 1,2,4-triazole and 1,3,4-oxadiazole derivatives
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A series of tetra-tert-butylcalix[4]arene linked to 1,2,4-triazole-5-thiones and 1,3,4-oxadiazole-5-thiones derivatives at lower rim were synthesized by the reaction of 1,2,4-triazole-5-thione and 1,3,4-oxadiazole-5-thione with 5,11,17,23-tetra-tert-butyl-25,27-bis(3-bromopropoxy)-26,28-dihydroxycalix[4]arene (2). The synthesized compounds were characterized by FT-IR, 1H NMR, 13C NMR spectral data, elemental analysis and ESI-MS.
- Ghezelbash, Zahra Dono,Dilmaghani, Karim Akbari
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p. 790 - 797
(2016/12/18)
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- Calix[4]arene-based low molecular mass gelators to form gels in organoalkoxysilanes
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Three calix[4]arene derivatives (CMA, CDA and CTA) appended with one, two or four carboxyl acid structures were prepared. Gelation behaviours of the compounds and calix[4]arene itself in ten common organoalkoxysilanes were studied. It was found that at a concentration of 2% (w/v), only the compound with the most carboxyl groups (CTA) functions as a gelator, and only this compound gels with three of the liquids tested; however, the as created gels possess smart thixotropic and thermo-reversible phase transition properties. In particular, the CTA/trimethoxyphenylsilane (PTMS) gel exhibits superior mechanical strength with a storage modulus (G′) greater than 1.9 × 106 Pa and a yield stress exceeding 3600 Pa at a concentration of 6.0% (w/v). Further testing demonstrated that the gel could be used as a substrate for sensing film fabrication, injection molding and melting-free deposition molding. Moreover, the objects from the molding and fabrication could be turned into permanent structures through further hydrolysis and condensation reactions. It is believed that the LMMGs based organoalkoxysilane gels have the potential to be used as smart materials for 3D printing and pre-cursors to a functionality-oriented solid matrix.
- Yang, Hui,Zhang, Shaofei,Liu, Kaiqiang,Fang, Yu
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p. 109969 - 109977
(2016/11/30)
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- First use of p-tert-butylcalix[4]arene-tetra-O-acetate as a nanoreactor having tunable selectivity towards cross azo-compounds by trapping silver ions
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p-tert-Butylcalix[4]arene-tetra-O-acetate was established for the first time as a member of the nanoreactor series, even without having any -OH group. The nano range distribution of this nanoreactor was ascertained by DLS, SEM and TEM studies. The capability of this cavitand towards hosting amines in a competitive manner generates a new green pathway for cross coupling of aromatic amines to give the corresponding azo-compounds. In this context, using p-tert-butylcalix[4]arene-tetra-O-acetate as a nanoreactor and silver nitrate as a catalyst, we got the cross azo-compound in good to excellent yields in the eco-friendly solvent water. This green methodology is also applicable for the synthesis of respective homo-compounds.
- Sarkar, Piyali,Mukhopadhyay, Chhanda
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supporting information
p. 442 - 451
(2016/01/30)
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- Synthesis and investigation of catalytic affinities of water-soluble amphiphilic calix[n]arene surfactants in the coupling reaction of some heteroaromatic compounds
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Six water-soluble calix[n]arene-based Br?nsted acid-type catalysts with amphiphilic groups were successfully synthesized by incorporating sulfonic acid moieties. Their structures were characterized using FTIR,1H NMR,13C NMR, APT-NMR, and elemental analysis techniques. Moreover, their catalytic capabilities were evaluated in the coupling reaction of 2-methylfuran and/or N-methylindole with some sec-alcohols in aqueous media. The association of their surfactant abilities, and the effects of water amount used and reaction durations on the catalytic activities of these amphiphilic calix[n]arene derivatives were also investigated. Observations indicated that these amphiphilic calix[n]arene catalysts exhibited high catalytic activities in the coupling reactions of 2-methylfuran and N-methylindole with some alcohols in water.
- Sayin, Serkan,Yilmaz, Mustafa
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p. 6528 - 6535
(2016/09/23)
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- The synthesis of new 8-imino-1-one acridine derivatives catalyzed by a calix[4]arene mono-acid core
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Mono-acid incorporated calix[4]arene has been successfully established as the catalyst for the synthesis of 8-imino-1-one acridine derivatives obtained by the condensation of enaminoketones and aldehydes (2:1 ratio). In this paper, we report the synthesis
- Sarkar, Piyali,Mukhopadhyay, Chhanda
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supporting information
p. 6556 - 6563
(2018/06/11)
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- Synthesis and C70 complexation studies of a fluorescent 5,5'-bi-p-tert-butylcalix[4]arene scaffold
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In this paper, we report the synthesis and C70 complexation studies of a new fluorescent 5,5'-bi-p-tert-butylcalix[4]arene capsule with an extended hydrophobic cavity. The synthetic route required development of a series of selective protection and de-pro
- Golan, Amos,Goldberg, Israel,Vigalok, Arkadi
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p. 526 - 535
(2016/04/19)
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