Studies on calix(aza)crowns, I. Synthesis, alkylation reactions and comprehensive NMR investigation of capped calix[4]arenes

Bitter, István; Grűn, Alajos; Tóth, Gábor; Balázs, Barbara; Tőke, Lásʐló

doi:10.1016/s0040-4020(97)00627-3

Cited by 63 publications

(30 citation statements)

References 24 publications

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“…Additionally, the flattening of the cone arising on alkylation is confirmed by the increase in the Dd(ArCH a H b Ar) value for 12-15 with respect to 10-11. [29] Slow evaporation of a solution of 14 in chloroform yielded crystals suitable for X-ray structure determination.…”

Section: Resultsmentioning

confidence: 99%

Bis(calixcrown)tetrathiafulvalene Receptors

Blesa

Zhao

Allain

et al. 2006

Chemistry A European J

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A new class of electroactive receptors has been synthesized, built by covalent association of five subunits: two calixarene platforms for spatial organization, two polyether 3D cavities for cation binding, and one electroactive TTF unit to probe the complexation event. Sodium complexation induces rigidification of the molecular assembly, as shown by 1H NMR titration and single-crystal X-ray crystallographic studies on free receptor 14 and a corresponding complex with two bound sodium atoms per receptor (15-(NaPF6)2). The calixarene units in these receptors change from a pinched cone conformation in the free ligand to a symmetrical cone in the complex. Cyclovoltammetric studies validated the electrochemical recognition concept of these five-member assemblies.

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Section: Resultsmentioning

confidence: 99%

Bis(calixcrown)tetrathiafulvalene Receptors

Blesa

Zhao

Allain

et al. 2006

Chemistry A European J

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“…Toluene-methanol solvent mixture was employed as toluene facilitates the dissolution of diester while methanol is beneficial to transforming the ethyl ester to the more reactive methyl ester prior to aminolysis. 50 The new compounds 3-7 were characterized by FTIR, 1 H NMR, spectra showed both characteristic amide and ester carbonyl bands about 1680 cm 21 and 1760 cm 21 , respectively. 1 H NMR spectra of the calix [4]arene diamide derivatives showed only the amide protons at 8.65-9.46 ppm, while IR spectra showed only characteristic amide bands about 1682 cm 21 and the disaappearance of ester carbonyl band at 1760 cm 21 .…”

Section: Results and Discussion Design And Synthesis Of The New Chiramentioning

confidence: 99%

Chiral mono and diamide derivatives of calix[4]arene for enantiomeric recognition of chiral amines

et al. 2007

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Novel chiral mono and diamide derivatives of calix[4]arene have been prepared from the aminolysis reaction of 5,11,17,23-tetra-tert-butyl-25,27-diethoxycarbonyl-methoxy-26,28-dihydroxycalix[4]arene 1 and 25,27-diethoxycarbonyl-methoxy-26,28-dihydroxycalix[4]arene 2 with chiral (S)-(-)-1-phenylethylamine (PEA) and (1S,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol, respectively. Spectrophotometric titrations have been performed in CHCl(3) at 20-30 degrees C in order to obtain the binding constants (K) and the thermodynamic quantities (DeltaH and DeltaS) for the stoichiometric 1:1 inclusion complexation of various chiral amines with these new host compounds. Preliminary experiments were undertaken to confirm the complexation properties of receptors 9 and 13 with PEA by (1)H NMR in CDCl(3) at room temperature. The molecular recognition abilities and enantioselectivities for guests (R and S)-alpha-PEA and (R and S)-cyclohexylethylamine (CHEA) are discussed from a thermodynamic point of view.

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“…Starting materials were commercially obtained and used without further purification. The synthesis of compounds 4-tert-butylcalix [4]arene, [34] 5,11,17,23-tetra-tert-butyl-25,27-diethoxycarbonylmethyloxycalix [4]arene, [9a,23] calix [4]azacrown 2, [35] and 5,17-di-tert-butyl-11,23-bis[(4Ј-methyl-2,2Ј-bipyridin-4-yl)carbonylamino]-25,27-bis(ethoxycarbonylmethoxy)calix [4]arene (13) [9a] and Ru II (bipy)Cl 4 [32] have been described in the literature previously.…”

Section: Methodsmentioning

confidence: 99%

Metal Complexation of Calix[4]azacrown Derivatives – Evidence for Communication Between Upper and Lower Functionalised Rims

Bond

Creaven²,

Donlon

et al. 2007

Eur J Inorg Chem

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The coordination chemistry of calix[4]azacrowns obtained from the reaction of a diester calix[4]arene with diethylenetriamine provided unusual copper(II) and manganese(II) complexes in which calix[4]azacrown acts as a bidentate N,O‐donor ligand, in some cases, but as a unidentate N‐donor ligand, in other cases. The first example of a binuclear ruthenium(II)/manganese(II) complex, involving the calix[4]arene framework as the bridging ligand, is also reported. The calix[4]arene framework consists of a bipyridyl unit connected at the upper rim of the calix[4]arene, through an amide linkage, and an azacrown unit at the lower rim, also connected through amide groups. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Studies on calix(aza)crowns, I. Synthesis, alkylation reactions and comprehensive NMR investigation of capped calix[4]arenes

Cited by 63 publications

References 24 publications

Bis(calixcrown)tetrathiafulvalene Receptors

Bis(calixcrown)tetrathiafulvalene Receptors

Chiral mono and diamide derivatives of calix[4]arene for enantiomeric recognition of chiral amines

Metal Complexation of Calix[4]azacrown Derivatives – Evidence for Communication Between Upper and Lower Functionalised Rims

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