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1.
A. P. Luk’yanenko E. A. Alekseeva S. S. Basok A. V. Mazepa A. I. Gren’ 《Russian Journal of Organic Chemistry》2011,47(4):527-529
A new procedure has been proposed for the synthesis of mono- and bis(2-aminoethoxy)-p-(tertbutyl) calix[4]arenes from the corresponding mono- and bis[2-(1,3-dioxoisoindol-2-yl)ethoxy]-p-(tert-butyl)-calix[4]arenes. 相似文献
2.
A series of p-tert-butylcalix[4]arene 1,3-diimidazolium salts were successfully prepared by the alkylation of p-tert-butylcalix[4]arene with dibromoalkanes, and sequential substitution reaction with 1-alkylimidazole. Furthermore, coordination reactions of p-tert-butylcalix[4]arene 1,3-diimidazolium salts with silver oxide and mercury acetate gave novel Ag and Hg complexes of bis(N-heterocyclic carbenes) on p-tert-butylcalix[4]arene platform. The single-crystal structures of four p-tert-butylcalix[4]arene 1,3-diimidazolium salts and three metal complexes were successfully determined by X-ray diffraction. An Ag–Ag argentophilic interaction (Ag–Ag bond length is 3.1599(6) Å) is formed between the two Ag–NHC complexes and a dimetallic coordination mode exists in Hg–NHC complexes. 相似文献
3.
Sreeja Thulasi Jisha Babu Adarsh Babukuttannair Viji Sreemathi Ramavarma Luxmi Varma 《Tetrahedron》2010,66(27-28):5270-5276
A seemingly ipso-like nucleophilic substitution of the upper rim of p-tert-butylcalix[4]arene is accomplished by an indirect method involving calix[4]arene derived bis(spirodienone). This method not only provides both mono and 1,3-diaryloxy calixarenes but also enables the synthesis of upper rim monothio substituted calix[4]arenes. A modification of the methodology can be successfully extended for the selective synthesis of mono- and 1,3-diquinone calix[4]arenes having free hydroxyl groups at the lower rim, in fewer steps. 相似文献
4.
Elena A. Alekseeva Aleksandr P. Luk’yanenko Andrei I. Gren 《Mendeleev Communications》2012,22(5):263-264
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-butylcalix[4]-arene in benzene or refluxing biscalixarene hydrazide in benzene in the presence of hydrazine hydrate produces the mixture of 1,2- and 1,3-(N,N’-diacetylhydrazine)-p-tert-butylcalix[4]arenes. 相似文献
5.
Özlem Özen Karakuş Hasalettin Deligöz 《Journal of inclusion phenomena and macrocyclic chemistry》2008,61(3-4):289-296
The synthesis of series of chromogenic di-substituted azocalix[4]arene derivatives is described. A ketone moiety as a different chelating agent is grafted on the lower rim of p-tert-butylcalix[4]arenes. Eight novel azocalix[4]arenes (1–8) are prepared by linking 2-, 3- and 4-nitroaniline, 4-phenylazoaniline, 3- and 4-chloroaniline or 2- and 4-methylaniline to 25,27-diacetonyloxy-26,28-dihydroxy-11,23-di-(tert-butyl)calix[4]arene through a diazo-coupling reaction, and characterized by UV–Vis, FT-IR and 1H-NMR spectroscopic techniques and elemental analysis, consecutively. The absorption spectra of the di-substituted azocalix[4]arenes are discussed, according to effect of varying pH and solvent upon the absorption ability of azocalix[4]arenes. The colors of these azocalix[4]arenes are compared with respect to nature of their aromatic rings and substituents there in. Concentration effects on the visible absorption maxima of these compounds are also reported. 相似文献
6.
A convenient procedure for direct introduction of one formyl group into p-tert-butylcalix[4]arenes through ipso substitution is described. 相似文献
7.
As bifunctional reagents, bis(tosyloxyethoxy)benzenes can react with p-tert-butylcalix[4]arene or p-tert-butylthiacalix[4]arene to afford intramolecularly bridged (1+1) or intermolecularly bridged (2+2) products. It was found that the bridging pattern strongly depended on the structure of bis(tosyloxyethoxy)benzene and the kind of calixarene. For the ortho-isomer of bis(tosyloxyethoxy)benzene, intramolecularly bridged calix[4]arene and thiacalix[4]arene were the main products. For the para-isomer, the bridging reaction was in a (2+2) fashion. As for the meta-isomer, double thiacalix[4]arene and intramolecularly bridged calix[4]crown were synthesized. 相似文献
8.
Serkan Erdemir Mustafa Yilmaz 《Journal of inclusion phenomena and macrocyclic chemistry》2012,73(1-4):141-150
Two novel chiral di- and tri-amide derivatives of p-tert-butylcalix[4]arene were synthesized by (R)-(+)-1-Phenylethylamine via convenient reactions and then immobilized on aminopropyl functionalized silica particles. The prepared chiral calix[4]arenes and their silica polymers (Calix-SP1 and Calix-SP2) were characterized using 1H NMR, 13C NMR, FT-IR, and thermal and elemental analysis techniques. 相似文献
9.
In the present work, the separations of calixarene derivatives have been investigated using both high-performance liquid chromatography (HPLC) and nonaqueous capillary electrophoresis (NACE) techniques. HPLC-1 method with LC-318 (pore size = 300 Å) column and MeCN mobile phase was optimized for the separation of calixarenes. At the flow-rate of 1 ml/min p-nitrocalix[6]arene, calix[4]arene and calix[6]arene could be well baseline and symmetrically separated within 5 min. For the separation of p-tert-butylcalix[n]arenes (n = 4, 6, 8), HPLC-2 and NACE methods have been optimized. The optimal conditions in HPLC-2 method included NH2 column and MeCN mobile phase, and p-tert-butylcalix[n]arenes (n = 4, 6, 8) were baseline separated within 10 min at 0.8 min/min. The optimal conditions for NACE method employed MeCN-H2O (8:2, v/v) as the nonaqueous medium and 120 mM Tris/HCl (pH 9.0) as the buffer, and p-tert-butylcalix[n]arenes (n = 4, 6, 8) were successfully baseline resolved within 16 min. With the detection at 280 nm, the calibration lines were linear in the ranges of 1-200 μg/ml for calixarene derivatives by HPLC-1 and HPLC-2 methods, and of 2.5-200 μg/ml for p-tert-butylcalix[n]arenes (n = 4, 6, 8) by NACE method, respectively. The detection limits (S/N = 3) and recoveries ranged from 0.5 to 1.4 μg/ml and from 98.1 to 102.4% by both HPLC-1 and HPLC-2 methods, and from 1.3 to 2.0 μg/ml and from 97.9 to 105.1% by NACE method, respectively. The intra-day reproducibility of the methods was determined with satisfactory results. The proposed HPLC and NACE methods were accurate and reproducible, and could be utilized to separate and determine calixarene derivatives. 相似文献
10.
Antipin I. S. Stoikov I. I. Khrustalev A. A. Konovalov A. I. 《Russian Chemical Bulletin》2001,50(11):2134-2143
A new type of macrocyclic receptor able to bind organic substrates containing carboxy and carboxylate groups was designed on the basis of 1,3-disubstituted calix[4]arenes. A series of disubstitited calix[4]arenes were prepared in 60—80% yields by selective 1,3-alkylation of p-tert-butylcalix[4]arene. The compounds obtained were tested as carriers for dl-tartaric, glycolic, dl-amygdalic, and dl-glutamic acids through liquid membranes immobilized on a polymer matrix. The structural factors favorable for the transport of these hydrophilic substrates through lipophilic membranes were established. 相似文献
11.
Emanuel Makrlík Michal ?ajan Jan Budka Petr Vaňura 《Monatshefte für Chemie / Chemical Monthly》2011,287(3):5-9
Abstract
Extraction experiments in the two-phase water/nitrobenzene system and γ-activity measurements were used to determine the stability constant of protonated tetrakis(2-ethoxyethoxy)-tetra-p-tert-butylcalix[4]arene in nitrobenzene saturated with water. Density functional theory (DFT) calculations were applied to derive the most probable structure of the tetrakis(2-ethoxyethoxy)-tetra-p-tert-butylcalix[4]arene·H3O+ complex species. 相似文献12.
I. V. Smirnov E. S. Stepanova N. M. Ivenskaya M. D. Karavan S. R. Zaripov S. E. Solovieva I. S. Antipin 《Doklady Chemistry》2018,479(1):36-40
Trends of cesium-137 and americium-241 extraction from carbonate–alkaline media with p-tert-butylcalix[n]arenes with macrocycles of different size (n = 4, 6, 8), including monofunctional derivatives with lipophilic substituents for increasing their solubility in organic media, were studied. It was demonstrated that O-n-octyl ethers of p-tert-butylcalix[6]arene appeared to be the most efficient extractants for Cs(I) cations, while it was p-tert-butylthiacalix[4]arene for and americium(III) cations. 相似文献
13.
Proximal heteroalkylation of monoalkyl ethers of calix[4]arenes or p-tert-butylcalix[4]arenes in NaH/CH3CN or NaOH/DMSO, respectively, was applied for synthesis of inherently chiral calixarenes with ABHH substitution pattern. The introduction by the method of (R)- or (S)-N-(α-phenylethyl)acetamide chiral auxiliary group gives mixtures of diastereomeric derivatives of inherently chiral calixarenes, which were separated by column chromatography. The chiral calixarenes were thoroughly characterized by 1H, 13C NMR, and X-ray diffraction methods. 相似文献
14.
Yoshihiko Kondo Ken Endo Nobuhiko Iki Sotaro Miyano Fumio Hamada 《Journal of inclusion phenomena and macrocyclic chemistry》2005,52(1-2):45-49
Even though it was obtained in poor yield, p-tert-butylthiacalix[8]arene (TC8A) has been synthesized as a new member of thiacalix[n]arenes by the terephthalate-induced cyclization of a mixture of acyclic oligomers, which was obtained by the reaction between p-tert-butylphenol and sulfur with CaO in ethylene glycol/diphenyl ether system. Slow evaporation of the chloroform solution of TC8A afforded guest-free crystals consisting of TC8A itself. The close-packed crystal structure of TC8A resembles that of p-tert-butylcalix[8]arene (C8A) closely, containing a plated loop molecular structure.This revised version was published online in July 2005 with a corrected issue number. 相似文献
15.
János B. Czirok Ákos Tarcsay Pál D. Mezei András Simon László Balázs 《Supramolecular chemistry》2013,25(10-12):722-728
The size limit of substituents allowing O-through-the-annulus rotation of substituted calix[4]arenes was further extended to the propargyloxy group in 24-propargyloxy-25,26,27-tris(N,N-dimethylcarbamoylmethoxy)-p-tert-butylcalix[4]arene by demonstrating its free but slow motion affording equilibrium between the partial cone and 1,2-alternate conformers. The effect of solvent and upper rim substituents R1 on the conformational inversion was investigated by means of 1H NMR. The rotational isomerisation of the parent (R1 = H) analogue could not unambiguously be detected. The experimental results were supported by comprehensive density functional theory studies. 相似文献
16.
Ivan I. Stoikov Arkadiy Yu. Zhukov Maria N. Agafonova Ruzal R. Sitdikov Igor S. Antipin Alexander I. Konovalov 《Tetrahedron》2010,66(1):359-14064
A series of new p-tert-butyl thiacalix[4]arenes with o-, m-, p-amido and o-, m-, p-(amidomethyl)pyridine substituents at the lower rim in cone, partial cone, and 1,3-alternate conformations were synthesized. The ability of the obtained compounds to recognize the α-hydroxy (glycolic, tartaric) and dicarboxylic (oxalic, malonic, succinic, fumaric, and maleic) acids was investigated by UV-vis spectroscopy. Also, the efficiency and selectivity of binding, the association constants log Ka (102 to 107 M−1) and the stoichiometry were determined for the complexes of p-tert-butyl thiacalix[4]arenes with the acids. The receptors based on p-tert-butyl thiacalix[4]arenes with (amidomethyl)pyridine substitutes are most efficient in complexation in many cases. 相似文献
17.
Ilenia Pisagatti Lucia Barbera Giuseppe Gattuso Salvatore Patanè Melchiorre F. Parisi 《Supramolecular chemistry》2018,30(8):658-663
Amphiphilic PEGylated calix[5]arenes 1 and 2 were obtained in one step from the parent p-tert-butylcalix[5]arene and p-methylcalix[5]arene. Very low critical micellar concentrations (0.5 and 4.5 μM for 1 and 2 respectively) were determined by the Rose Bengal micellization method. Aggregation features were studied by means of 1H and DOSY NMR as well as by AFM. Release of Rose Bengal from the micellar environment was accomplished by increasing the temperature. 相似文献
18.
E. A. Alekseeva S. S. Basok A. V. Mazepa A. P. Luk’yanenko O. V. Snurnikova A. I. Gren’ 《Russian Journal of General Chemistry》2013,83(9):1738-1743
A series of disubstituted p-tert-butylcalix[4]arenes with N-methoxycarbonylmonoazacrown ether and N-ethoxymonoazacrown ether residues at the lower rim has been prepared via the reaction of di(carboxymethoxy)-p-tert-butylcalix[4]arene with azacrown ethers and subsequent reduction of the resulting amide derivatives. Using UV titration and 1H NMR spectroscopy we have demonstrated the ability of the calixarene with two N-carbonylmonoaza-18-crown-6-ether substituents to form the 1:3 complexes with K+ and Na+ and the 1:2 complexes with Cs+, Sr2+, Cu2+, and Zn2+. The calixarene with two fragments of N-ethoxymonoazo-18-crown ether has formed binuclear complexes with alkali metals cations and mononuclear complexes with transition metals cations. 相似文献
19.
I. DUMAZET N. Ehlinger F. VOCANSON S. Lecocq R. LAMARTINE M. Perrin 《Journal of inclusion phenomena and macrocyclic chemistry》1997,29(2):175-185
The formation of p-tert-butylcalix[5]arene by the opening ofp-tert-butyldihomooxacalix [4]arene and the addition of a monomer has beenstudied. Various facets, including the effects of bases and the nature ofthe monomer added to the p-tert-butyldihomooxacalix[4]arene, have beeninvestigated. p-tert-Butylcalix[5]arene can be prepared in yields up to30%. The structure of its 1 : 2 complex with DMF has been determinedby X-ray crystallography. Crystals are triclinic, space group P¯1, a =1428.2(3) pm, b = 1837.3(3) pm, c = 1276.1(2) pm, = 108.98(1)°, = 105.02(2)°, = 95.21(1)°, Z = 2, D c = 1.059 kg m-3,final R value = 0.087. The macrocycle adopts a cone conformation, one guestenclosed inside the cavity, the other one outside. 相似文献