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1.
Hasalettin Deligöz 《Supramolecular chemistry》2013,25(5):317-321
Five new polymeric compounds containing more than one calix[4]arene have been synthesized by reacting an oligomer with 5,11,17,23-tetrakis[(diethylamino)methyl]-25,26,27,28-tetrahydroxycalix[4]arene (L1), 25,27-dimethyl-26,28-dihydroxy-p-tert-butylcalix[4]arene diketone (L2), and p-nitrocalix[4]arene (L3), and chloromethylated polystyrene with 25,27-dimethyl-26,28-dihydroxy-p-tert-butylcalix[4]arene diketone (L4) and p-nitrocalix[4]arene (L5). These compounds were studied by the selective extraction of Fe3+ cation from the aqueous phase into the organic phase and was carried out by using compounds L1–L5. It was observed that the polymer support attached to the lower rim of p-nitrocalix[4]arene was the most efficient carrier of Fe3+ in the extraction process. 相似文献
2.
Korakot Navakun Thawatchai Tuntulani Vithaya Ruangpornvisuti 《Journal of inclusion phenomena and macrocyclic chemistry》2000,38(1-4):113-122
25,27(2,2'-bis(ethoxybenzyl))-1,9-diimine-3,7-dithianonane-p-tert-butylcalix[4]arene (3),25,27(4,4'-bis(ethoxybenzyl))-1,9-diimine-3,7-dithianonane-p-tert-butylcalix[4]arene (4),25,27(2,2'-bis(ethoxybenzyl))-1,8-diimine-3,6-dithianonane-p-tert-butylcalix[4]arene (5) and25,27(4,4'-bis(ethoxybenzyl))-1,8-diimine-3,6-dithianonane-p-tert-butylcalix[4]arene (6) havebeen synthesized by condensation reactions between25,27(2,2'-bis(ethoxybenzaldehyde))-p-tert-butylcalix[4]arene (1) and25,27(4,4'-bis(ethoxybenzaldehyde))-p-tert-butylcalix[4]arene (2) and appropriateamines. Reduction of 3 and 4 withNaBH4 and subsequent protonation byHCl/CH3OH resulted in25,27(2,2'-bis(ethoxybenzyl))-1,9-diaza-3,7-dithianonane-p-tert-butylcalix[4]arenedihydrogenchloride (7) and25,27(4,4'-bis(ethoxybenzyl))-1,9-diaza-3,7-dithianonane-p-tert-butylcalix[4]arenedihydrogenchloride (8), respectively. Complexation studies of 7 and 8 withZn(II), Cd(II) and Hg(II) ions were carried out bypotentiometric titration. Compounds 7 and8 selectively form 1 : 1 complexes with Hg(II), andtheir stability constants (log Ks) were estimated tobe 4.47 ± 0.08 and 3.20 ± 0.13, respectively. From spiecies distribution plots, 7 and 8were found to form the highest amount of 1 : 1 complexes with Hg(II) at pH 8.7 and 9.1, respectively. 相似文献
3.
Rossella Ferro Consiglia Tedesco Carmine Gaeta Placido Neri 《Journal of inclusion phenomena and macrocyclic chemistry》2005,52(1-2):85-91
The first example of a calix[8]quinone derivative, hexamethoxy-p-tert-butylcalix[8]-1,5-diquinone 5, has been synthesized from p-tert-butylcalix[8]arene 1by exploiting a protection-deprotection procedure. The structure of the 5·toluene inclusion compound has been determined by a single crystal X-ray diffraction study. The calix[8]arene molecule possesses a crystallographic inversion centre and assumes a ‘pseudo-chair-like’ conformation, with two opposite 3/4-cone moieties, which resembles the previously reported chair-like conformation of p-tert-butylcalix[8]arene. The 4 toluene molecules per unit cell occupy interstitial voids and are released in the temperature range of 30–160 °C.This revised version was published online in July 2005 with a corrected issue number. 相似文献
4.
Ratana Seangprasertkij Zouhair Asfari Françoise Arnaud Jean Weiss Jacques Vicens 《Journal of inclusion phenomena and macrocyclic chemistry》1992,14(2):141-147
This communication describes the synthesis of Schiff base calix[4]arene (1) in which the Schiff base unit bridges two opposite hydroxy groups ofp-tert-butylcalix[4]arene. The synthesis of (1) has been achieved by refluxing in acetonitrile-methanol the appropriate 1,3-dicarbaldehyde-p-tert-butyl-calix[4]arene (4) with 1,3-diaminopropane. The yield of the reaction is 19%. Ligand (1) possesses a compartment containing two nitrogen atoms, four ether-type oxygen atoms, and two ionizable hydroxy groups likely to complex metal cations. 相似文献
5.
Haibing Li Dejun Xiong Yuanyin Chen Peng Xie Jian Wan 《Journal of inclusion phenomena and macrocyclic chemistry》2008,60(1-2):169-172
p-tert-Butylcalix[7]arene reacting with phosphorus pentachloride and then with water afforded two stereoisomers p-tert-butylcalix[7]arene diphosphates 2a and 2b, representing the first phosphorus multiple bridged calix[7]arene. The more accurate structure of 2a was investigated with
the aid of Gaussian03 calculations. 相似文献
6.
Saleh A Ahmed Mutsuo Tanaka Hisanori AndoHitoshi Iwamoto Keiichi Kimura 《Tetrahedron》2003,59(23):4135-4142
Novel t-butylcalix[4]arenes bearing several chromene molecules were synthesized, and their photochromism and metal-ion binding ability were examined with alkali and alkaline-earth metal ions. While the metal-ion binding ability of the t-butylcalix[4]arene moiety facilitated the photoisomerization of the chromene moiety to a great extent, the chromene moiety influenced the metal-ion binding ability of the t-butylcalix[4]arene moiety through lariat effect. Therefore, the metal-ion that induced the most facilitated photoisomerization of the chromene moiety was shifted drastically from Li+ to Ba2+ with the increase of the incorporated chromene number. Even without metal ions, the interaction among the chromene moieties derived from the cone-conformation of the t-butylcalix[4]arene moiety also facilitated the photoisomerization. 相似文献
7.
8.
Mouna Ferchichi Erwann JeanneauBernard Fenet Faouzi MeganemUlrich Darbost Isabelle Bonnamour 《Tetrahedron letters》2012,53(32):4047-4050
The synthesis of a series of six new per-substituted p-tert-butylcalix[9]arenes derivatives has been achieved. Functions such as ester, nitrile, or carbonate have been grafted on the phenolic oxygens of calix[9]arene: p-tert-butylcalix[9]arene nona-ethyl acetate, p-tert-butylcalix[9]arene nona-carboxylic acid, p-tert-butylcalix[9]arene nona-cyanopropyloxy, p-tert-butylcalix[9]arene nona-tert-butoxycarbonyle, p-tert-butylcalix[9]arene nona-acetyl, and p-tert-butylcalix[9]arene nona-trifluoroacetyl have been obtained in good yields (from 48% to 78%) and fully characterized. The X-ray structures of p-tert-butylcalix[9]arene nona-tert-butoxycarbonyl and p-tert-butylcalix[9]arene nona-ethyl acetate have been determined. A dynamic NMR study has revealed the high conformational mobility of such structures, even at low temperature. 相似文献
9.
Paula M. Marcos José R. Ascenso Manuel A.P. Segurado J.L.C. Pereira 《Journal of inclusion phenomena and macrocyclic chemistry》2002,42(3-4):281-288
The binding properties of two phenylketones (2a and 3a) and two ethylesters (2b and {3b) derived from p-tert-butyldihomooxacalix[4]arene or from p-tert-butylcalix[4]arene, in the cone conformation, towards transition (Ag+, Ni2+, Cu2+, Co2+, Zn2+, Fe2+ and Mn2+) and heavy (Cd2+, Hg2+ and Pb2+) metal cations have been determined by extraction studies with metal picrates and liquid membrane transport experiments with the same salts. The affinity of these ligands for Ag+ has also been investigated by 1H NMR spectroscopy. Both ketones are better extractants than the esters, and show a strong preference for Ag+, while Cu2+ is the most extracted cation with the esters. 1H NMR titrations with AgSO3CF3 indicate 1 : 1 complexes for all ligands, those with ketones are more stable, on the NMR time scale, than those with esters. Both esters are good carriers for Ag+, and 2b exhibits the highest transport rate (4.7 mol h-1) found until now with dihomooxacalix[4]arene derivatives. 相似文献
10.
Paula M. Marcos Filipa A. Teixeira Manuel A.P. Segurado José R. Ascenso Raul J. Bernardino Peter J. Cragg 《Supramolecular chemistry》2013,25(8):522-532
The binding of lanthanide cations by 2-pyridylmethoxy derivatives of p-tert-butyldihomooxacalix[4]arene (1b), in the cone conformation, and p-tert-butylhexahomotrioxacalix[3]arene (2b), in both cone and partial cone conformations, was studied. These properties were assessed by extraction studies of the metal picrates from water into dichloromethane and stability constant measurements in methanol and acetonitrile, using spectrophotometric and microcalorimetric techniques. Proton NMR titrations with La3+ and Yb3+ cations were done in order to get information on the binding sites. Computational methods (density functional theory (DFT) calculations) were also used to complement the NMR data. The p-tert-butylcalix[4]arene analogue (3b) was also studied, and the results of the four ligands were compared. Partial cone-2b is the best extractant for lanthanide ions, showing some preference for the heavy lanthanides. In complexation, all four ligands show the same trend and a high selectivity for Yb3+ (ML, log β ≥ 7). Besides the formation of ML complexes, ML2 species were also obtained. In most cases, these species were corroborated by the proton NMR studies. For partial cone-2b with Pr3+ the complexation process is enthalpically driven, whereas for 3b the formation of the ML2 species with this cation is due to a favourable entropy term. DFT studies indicate that ligand 3b forms the most stable complex with La3+, followed by partial cone-2b. 相似文献
11.
Fafu Yang Biqiong Hong Xianfeng Chai Fengju Yin Yuanyin Chen 《Supramolecular chemistry》2013,25(8):691-698
By reacting mono-substituted or 1,3-bi-substituted [2-(p-formylphenyloxy)ethyloxy]-p-tert-butylcalix[4]arene (3 or 4) with hydrazine hydrate in ‘1+2’ or ‘2+2’ condensation mode, novel benzalazine-bridging biscalix[4]arenes 5 and 7 were conveniently obtained in the yields of 76 and 81%, respectively. Condensation of compound 4 and salicylide hydrazone gave a novel calix[4]arene benzalazine derivative 6 in the yield of 85%. The structures and conformations of all new compounds were characterised by elemental analyses, ESI-MS, 1H NMR and 1H–1H COSY techniques. Biscalix[4]arene 7 adopts a symmetrical cone conformation with tube cavity. The liquid–liquid extraction experiment showed that all new hosts possessed excellent complexation abilities towards soft metal cations. Compound 7 exhibited high complexation selectivity towards Ag+. The Ag+/Na+ and Ag+/Hg2+ extraction percentages of host 7 were as high as 73.1 and 54.9, respectively. The UV–vis spectra complexation experiments revealed that the complexation constant of receptor 7 with Ag+ was 1.9 × 105 M? 1 and the 1:1 stoichiometry of receptor 7–Ag+ complex was formed. The 1H NMR spectra complexation experiments suggested that Ag+ was bound in a cavity composed of two benzalazine groups on bridging chains. 相似文献
12.
Mine Sulak Ak Hasalettin Deligöz 《Journal of inclusion phenomena and macrocyclic chemistry》2007,59(1-2):115-123
Four new azocalix[4]arenes {5,11,17,23-tetrakis[(2-hydroxy-5-tert-butylphenylazo)]-25,26,27,28-tetrahydroxycalix[4]arene (1), 5,11,17,23-tetrakis[(2-hydroxy-5-nitro phenylazo)]-25,26,27,28-tetrahydroxycalix[4]arene (2), 5,11,17,23-tetrakis[(2-amino-5-carboxylphenylazo)]-25,26,27,28-tetrahydroxycalix[4]arene (3) and 5,11,17,23-tetrakis[(1-amino-2-hydroxy-4-sulfonicacidnapthylazo)]-25,26,27,28-tetrahydroxycalix[4]arene (4)} have been synthesized from p-tert-butylphenol, p-nitrophenol, p-aminobenzoic acid and 1-amino-2-hydroxy-4-sulphonic acid by diazo coupling reaction with p-aminocalix[4]arene. The resulting ligands (1–4) were treated with three transition metal salts (e.g., CuCl2·2H2O, NiCl2·6H2O or CoCl2·6H2O). Cu(II), Ni(II) and Co(II) complexes of the azocalix[4]arene derivatives were obtained and characterized by UV-vis, IR,
1H-NMR spectroscopic techniques and elemental analysis. All the complexes have a metal:ligand ratio of 2:1. The Cu(II) and
Ni(II) complexes of azocalix[4]arenes are square-planar, while the Co(II) complexes of azocalix[4]arenes are octahedral with
water molecules as axial ligands. The solvent extraction of various transition metal cations from the aqueous phase to the
organic phase was carried out by using azocalix[4]arenes (1–4). It was found that, azocalix[4]arenes 1, 2 and 3 examined selectivity for transition metal cations such as Ag+, Hg+ and Hg2+. In addition, the thermal stability of metal:azocalix[4]arene complexes were also reported.
Dedicated to Prof. Dr. Mustafa Yılmaz on the occasion of his 50th birthday 相似文献
13.
Yanfei Yang Xiaodan Cao Kazimierz Surowiec Richard A. Bartsch 《Journal of inclusion phenomena and macrocyclic chemistry》2010,66(1-2):163-169
A regioisomer of a previously reported p-tert-butylcalix[4]arene-1,3-thiacrown-5 di(carboxylic acid) is prepared in which the thiacrown ring attachment sites are moved from distal phenolic oxygens of a cone p-tert-butylcalix[4]arene scaffold to proximal phenolic oxygens. The influence of this structural variation in the di-ionizable calixcrown ligand on competitive solvent extractions of alkali metal cations and of alkaline earth metal cations and single species solvent extractions of Hg2+ and Pb2+ from aqueous solutions into chloroform is evaluated. 相似文献
14.
C. David Gutsche Alice E. Gutsche Alexander I. Karaulov 《Journal of inclusion phenomena and macrocyclic chemistry》1985,3(4):447-451
Monoclinic prisms were obtained by slow evaporation of a pyridine solution ofp-tert-butylcalix[8]arene: space groupP21/c,a=20.312(3),b=23.020(2),c=20.006(6) ; =113.05(2)0;V=8707.6 Å3;Z=4. Refinement led to anR value of 0.166 for 4231 reflections which, although high, is sufficient to establish the conformation of the molecule as a pleated loop in which the eight hydroxyl groups are arranged in a slightly undulating, almost planar, intramolecularly hydrogen bonded cyclic array. The possible inferences for the conformation ofp-tert-butylcalix[8]arene in solution are discussed.
Supplementary Data relating to this article are deposited with the British Library as Supplementary Publication No. SUP 82019. 相似文献
15.
Emanuel Makrlík Ji?í Dybal Petr Vaňura 《Monatshefte für Chemie / Chemical Monthly》2009,286(1):1289-1292
Abstract From extraction experiments in the two-phase water–nitrobenzene system and γ-activity measurements, the stability constant
of protonated tetraethyl p-tert-butylcalix[4]arene tetraacetate in nitrobenzene saturated with water was determined. By using DFT calculations, the most
probable structure of the tetraethyl p-tert-butylcalix[4]arene tetraacetate·H3O+ complex species was derived.
Graphical Abstract
相似文献
16.
Francine F. Nachtigall Eduardo Ernesto Castellano Faruk Nome 《Supramolecular chemistry》2013,25(6):453-458
The interactions of calix[6]arene and p-tert-butylcalix[6]arene with aliphatic amines in acetonitrile solution were studied by spectrophotometric titrations in the UV region and 1H NMR spectrometry. Calix[6]arenes can undergo two deprotonations by aliphatic amines and the extent of the second proton transfer is mainly governed by the size of the α-substituent of the amine. 1H NMR spectra show that the macrocycle adopts a 1,2,3-alternate conformation and that the α-hydrogens of the ammonium ions are shielded by the π-clouds of the aromatic rings. The X-ray crystal structure of the dihexylammonium complex of the p-tert-butylcalix[6]arene dianion, reported here, confirms the 1,2,3-alternate conformation and shows one of the two ammonium moieties encapsulated in the inner cavity of the macrocycle. 相似文献
17.
Abstract The synthesis and full characterization of eight new calix[n]arene sulfonate esters including their conformational analysis were carried out. While p-tBucalix[6]arene and p-tBu-calix[8]arene esters are conformationally labile in the temperature interval of 25–100°C, p-tBu-calix[4]arene mono-and diesters were isolated as stable conformers at ambient temperature. Two 1,3-functionalised compounds of these derivatives, p-tert-butylcalix[4]arene ditriflate (5) and dimesylate (6) were shown unexpectedly high conformational stability up to 100°C by dynamic NMR measurements. The NMR measurements confirm the pinched-cone conformation for both derivatives. For the dealkylated calix[4]arene derivatives the partial cone conformer of the triesters have been obtained as major products in all cases. 相似文献
18.
Bang-Tun Zhao Xiao-Min Zhu Qi-Ming Peng Zhen-Ning Yan Franck Le Derf Marc Sallé 《Central European Journal of Chemistry》2011,9(6):1102-1108
A novel redox-active calix[4]arene-TTF 5 was prepared by the reaction of p-tert-butylcalix[4]arene 4 with the tosylated TTF 3 in the presence of cesium fluoride. The structure of the dyad 5 was identified by X-ray diffraction analysis, and the preliminary electrochemical properties of 5 were investigated by cyclic voltammetry (CV), for which two reversible one-electron waves were observed. Moreover, the UV-vis
absorption spectra studies show that the dyad 5 undergoes progressive oxidation at the TTF moiety in presence of increasing amounts of Cu2+ or Hg2+.
相似文献
19.
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
20.
Ryan T. Chester Roland de Marco Mauro Mocerino Brian W. Skelton Allan H. White 《Supramolecular chemistry》2013,25(6):479-485
The tetra-isopropyl ethers of calix[4]arene and p-t-butylcalix[4]arene have been isolated in the cone conformation, and structurally characterised as chloroform solvates. Thermogravimetric analysis demonstrated that the parent isopropylcalix[4]arene solvate is significantly more stable than the p-t-butylcalix[4]arene analogue, retaining the solvent up to a temperature of 125°C. It was found that the calix[4]arene ether sublimes at atmospheric pressure, and solvent-free crystals appropriate for structure determination were produced at reduced pressure. The p-t-butylcalix[4]arene ether was also isolated without solvent in the lattice, but in this case the calixarene was crystallised from acetone, as sublimation did not produce crystals of sufficient quality. 相似文献