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Crystal structure of a mono-bridged calix[4]arene.

ABSTRACT: The title compound, 5(2)-[(5-bromo-pent-yl)-oxy]-1(2),1(14),3(5),5(5)-tetra-tert-butyl-1(7),1(8),1(9),1(10)-tetra-hydro-1(6) H,1(16) H-1(4,12)-dibenzo[b,e][1,7]dioxa-cyclo-dodecina-3,5(1,3)-dibenzena-cyclo-hexa-phan-3(2)-ol, C54H73BrO4, was synthesized from the reaction of tert-butyl-calix[4]arene with 1,5-di-bromo-pentane using K2CO3 in CH3CN. The structure consists of a calixarene unit with a five-carbon bridge connecting two proximal phenolic O atoms, and with a bromo-pent-oxy chain on one of the remaining phenolic O atoms. The calixarene unit was found to have a flattened cone conformation with no solvent (or other guest) mol-ecule observed in the cavity. Two of the opposite phenyl rings lean outwards with fold angles of 136.2 (1) and 133.0 (1)° between the rings and the plane of the bridging methyl-ene C atoms, while the other two opposite rings form fold angles of 83.27 (9) and 105.46 (9)°. There is considerable disorder in this mol-ecule. One of the tert-butyl groups is disordered over two conformations with occupancies of 0.527 (5) and 0.473 (5). The bromo-pent-oxy chain is disordered over three configurations with occupancies of 0.418, 0.332 and 0.250. The five-carbon bridge connecting two proximal phenolic O atoms is disordered over two conformations with occupancies of 0.537 (7) and 0.463 (7).

SUBMITTER: Hailu ST

PROVIDER: S-EPMC4518971 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure of a supra-molecular lithium complex of p-tert-butyl-calix[4]arene.

Project description:Crystals of a supra-molecular lithium complex with a calix[4]arene derivative, namely tetra-methano-llithium 5,11,17,23-tetra-tert-butyl-25,26,27-trihy-droxy-28-oxidocalix[4]arene methanol monosolvate, [Li(CH3OH)4](C44H55O4)·CH3OH or [Li(CH3OH)4]+·(calix[4]arene-)]·CH3OH (where calix[4]arene- represents a mono-anion species because of deprotonation of one H atom of the calixarene hy-droxy groups), were obtained from p-tert-butyl-calix[4]arene reacted with LiH in tetra-hydro-furan, followed by recrystallization from methanol. The asymmetric unit comprises one mono-anionic calixarene mol-ecule, one Li+ cation coordinated to four methanol mol-ecules, and one methanol mol-ecule included in the calixarene cavity. The calixarene mol-ecule maintains a cone conformation by intra-molecular hydrogen bonding between one phenoxide (-O-) and three pendent calixarene hy-droxy groups (-OH). The coordinated methanol mol-ecules around the metal cation play a significant role in forming the supra-molecular assembly. The crystal structure of this assembly is stabilized by three sets of inter-molecular inter-actions: (i) hydrogen bonds involving the -OH and -O- moieties of the calixarene mol-ecules, the -OH groups of the coordinated methanol mol-ecules, and the -OH group of the methanol mol-ecule included in the calixarene cavity; (ii) C-H?? inter-actions between the calixarene mol-ecules and/or the coordinated methanol mol-ecules; (iii) O-H?? inter-actions between the calixarene mol-ecule and the included methanol mol-ecule.

| S-EPMC5947466 | biostudies-literature

Synthesis, Crystal Structure, and Biological Activity of a Multidentate Calix[4]arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone.

Project description:The design and synthesis of a novel tert-butyl-calix[4]arene functionalized at 1, 3 positions of the lower rim with two terminal 2-hydroxybenzeledene-thiosemicarbazone moieties is reported. The new ligand with multi-dentate chelating properties was fully characterized by several techniques: ESI-Mass spectroscopy, FT-IR, 1H-NMR, and single crystal X-ray diffraction. The solid state structure confirms that the calix[4]arene macrocycle has the expected open cone conformation, with two opposite phenyl rings inclined outwards with large angles. The conformation of the two alkoxythiosemicarbazone arms produces a molecule with a C2 point group symmetry. An interesting chiral helicity is observed, with the two thiosemicarbazone groups oriented in opposite directions like a two-blade propeller. A water molecule is encapsulated in the center of the two-blade propeller through multiple H-bond coordinations. The antibacterial, antifungal, anticancer, and cytotoxic activities of the calix[4]arene-thiosemicarbazone ligand and its metal derivatives (Co2+, Ni2+, Cu2+, and Zn2+) were investigated. A considerable antibacterial activity (in particular against E. coli, MIC, and MBC = 31.25 μg/mL) was observed for the ligand and its metal derivatives. Significant antifungal activities against yeast (C. albicans) were also observed for the ligand (MIC = 31.25 μg/mL and MBC = 125 μg/mL) and for its Co2+ derivative (MIC = 62.5 μg/mL). All compounds show cytotoxicity against the tested cancerous cells. For the Saos-2 cell line, the promising anticancer activity of ligand L (IC50 < 25 μg/mL) is higher than its metal derivatives. The microscopic analysis of DAPI-stained cells shows that the treated cells change in morphology, with deformation and fragmentation of the nuclei. The hemo-compatibility study demonstrated that this class of compounds are suitable candidates for further in vivo investigations.

| S-EPMC7024204 | biostudies-literature

Ion pair-induced conformational motion in calix[4]arene-strapped calix[4]pyrroles.

Project description:In order to understand the still-poorly understood interplay between calix[4]arene conformations and cation and anion recognition in multicomponent systems, the ion pair receptors 1 and 2 were synthesized. In solution and in the solid state, the calix[4]arene subunit of receptor 1 adopts a cone conformation, while that of 2 interconverts between the cone and the partial cone conformation. These geometric features differ from previous systems where the calix[4]arene moiety was locked in the 1,3-alternate conformation. A combination of 1H NMR spectroscopic analyses and single crystal X-ray diffraction studies reveal that receptor 1 binds the fluoride and the chloride anion via significantly different binding modes, displaying, for instance, 1 : 1 and 2 : 3 binding stoichiometries with CsF and CsCl, respectively. In the case of 2, the conformation of the calix[4]arene constituent of 2 is highly dependent on the size and quantity of anions present. For example, upon treatment of 2 with the fluoride anion (as both the TBA+ and Cs+ salts), the calix[4]arene unit coexists as cone and partial cone conformers that are inter-convertible. In the presence of excess CsF, the aromatic rings of the calix[4]arene subunit becomes locked in the pinched cone conformation with the result that an ion pair-mediated coordination polymer is formed. In the presence of excess CsCl, the calix[4]arene unit of 2 adopts only the partial cone conformation stabilized by aryl CH-anion hydrogen bonding interactions. The present systems constitute a rare set of related receptors wherein the effects of conformational changes are so tightly coupled with ion recognition.

| S-EPMC5811093 | biostudies-literature

5,11,17,23-Tetra-kis(1,1-di-methyl-eth-yl)-26,28-di-hydroxy-calix[4]arene-25,27-mono-thia-crown-3.

Project description:The title calix[4]arene compound [systematic name: 3,9,15,34-tetra-tert-butyl-19,29-dioxa-24-thia-hexa-cyclo-[15.13.7.1(7,11).1(32,36).0(5,30).0(13,18)]nona-triaconta-1(30),2,4,7,9,11(39),13,15,17,32,34,36(38)-dodeca-ene-38,39-diol], C52H70O4S, displays a cone-like conformation, the opposite arene rings bridged by the mono-thia-crown-3 unit are nearly parallel [dihedral angle = 16.01?(18)°], whereas the other opposite arene rings are twisted to each other at an angle of 74.41?(17)°. Intra-molecular O-H?O hydrogen bonds help to stabilize the mol-ecular structure. In the crystal, a C-H?? inter-action occurs. One of the tert-butyl groups is disordered over two sets of sites with a site-occupancy ratio of 0.70:0.30.

| S-EPMC3647882 | biostudies-other

Calix[6]arene-based atropoisomeric pseudo[2]rotaxanes.

Project description:Some examples of atropoisomeric pseudorotaxanes in which the isomerism arises by the different conformations adopted by the wheel are reported here. Upon threading hexahexyloxycalix[6]arene 1 with ammonium axles 2+ or 3+ , bearing biphenyl or trifluoromethylbenzyl moieties, respectively, two atropoisomeric pseudorotaxanes were formed in which the calix[6]-wheel 1 adopts the 1,2,3-alternate and cone conformations. The interconversion between them cannot be obtained by simple rotation around the ArCH2Ar bonds of the calixarene wheel, which is blocked by the presence of the axle inside its cavity. Therefore, it can only be obtained through a mechanism of de-threading/re-threading of the axle. In all the examined cases, the 1,2,3-alternate and cone atropoisomers are, respectively, the kinetic and the thermodynamic ones.

| S-EPMC6122310 | biostudies-literature

5,17-Diformyl-25,26,27,28-tetra-propoxy-calix[4]arene.

Project description:The title compound, C42H48O6, was obtained via formyl-ation of 25,26,27,28-tetra-propoxycalix[4]arene with dichloro-methyl methyl ether and tin tetra-chloride. It adopts a pinched cone conformation, which leads to an open cavity. The two opposite aromatic rings bearing formyl groups are almost parallel, making a dihedral angle of 29.1?(2)°. The other pair of opposite rings are close to being perpendicular, making a dihedral angle of 73.6?(1)°. Adjacent rings are almost perpendicular, making dihedral angles of 78.8?(2), 81.6?(1), 78.2?(1) and 74.7?(1)°.

| S-EPMC3588550 | biostudies-other

Multiple threading of a triple-calix[6]arene host.

Project description:The synthesis of the triple-calix[6]arene derivative 6 in which three calix[6]arene macrocycles are linked to a central 1,3,5-trimethylbenzene moiety is reported. Derivative 6 is able to give multiple-threading processes in the presence of dialkylammonium axles. The formation of pseudo[2]rotaxane, pseudo[3]rotaxane, and pseudo[4]rotaxane by threading one, two, and three, respectively, calix-wheels of 6 has been studied by 1D and 2D NMR, DOSY, and ESI-FT-ICR MS/MS experiments. The use of a directional alkylbenzylammonium axle led to the stereoselective formation of endo-alkyl pseudo[n]rotaxane stereoisomers.

| S-EPMC6753684 | biostudies-literature

Structural analysis of a calix[4]arene-based Platonic Micelle.

Project description:We have recently introduced the concept of "Platonic micelles", the preference of spherical micelles to specific aggregation numbers mostly coinciding with the number of faces of platonic solids. This effect was observed on bulky, mostly calix[4]arene-based surfactant systems with small aggregation numbers. The preferred aggregation numbers result in better sphere coverage, highliting the packing and the "protection" of hydrophobic cores from the aqueous solvent as the most important factor for this preference. In the present study we further explore the interactions that drive the packing of the highly charged PACaL3 surfactant into highly symmetrical hexameric micelles. We performed a series of molecular dynamics simulations that yielded a large set of structures and an ensemble in good agreement with the experimental Small Angle X-ray Scattering data was selected. The geometry and the rigidity of the calix[4]arene group with proper tail length and headgroup volume are the driving forces for the high symmetry and monodispersity of the micelle. The charge of the headgroups is mainly responsible for inhibiting the formation of higher order structures. Sodium, shown to be important for the stability of the micelle, is not directly interacting with the micelle implying that the calix[4]arene ring is a C2? symmetry conformation.

| S-EPMC6374510 | biostudies-literature

25,26,27,28-Tetra-kis(3-bromo-benzyl-oxy)calix[4]arene.

Project description:In the title compound, C(56)H(44)Br(4)O(4), the calix[4]arene unit displays the 1,2-alternate conformation with crystallograpically imposed inversion symmetry. The four phen-oxy rings of the calix[4]arene unit are twisted about the mean plane defined by the four methyl-ene C atoms bridging the benzene rings, with dihedral angles of 46.73?(6) and 66.11?(5)°. The dihedral angle between adjacent phen-oxy rings is 74.75?(7)°. The two pendant bromo-phenyl rings on the same side of the calix[4]arene unit are nearly perpendicular to each other, with a dihedral angle of 72.85?(10)° due to an intra-molecular C-H?? inter-action. In the crystal, a Br?Br contact of 3.6350?(5)?Å, an inter-molecular C-H?Br hydrogen bond and an inter-molecular C-H?? inter-action are observed.

| S-EPMC3151756 | biostudies-literature

Hydrogen-Bridged Oligosilanylsilyl Mono- and Oligosilanylsilyl Dications.

Project description:Hydrogen-bridged oligosilanylsilyl borates 8 [B(C6 F5 )4 ], 9[B(C6 F5 )4 ] and diborates 10 [B(C6 F5 )4 ]2 have been prepared by hydride transfer between α-ω-dihydrido- (11) and branched tetrahydrido-oligosilanes (13) and trityl cation. The obtained cyclic intramolecularly stabilized silylium ions 8, 9 and bissilylium ion 10 were characterized by low temperature NMR spectroscopy supported by the results of density functional calculations. The branched Si-H-Si monocation 9 undergoes at low temperatures a fast degenerate rearrangement, which exchanges the Si-H groups with a barrier of 31 kJ mol-1 via an antarafacial transition state. Reaction of the branched monocation 9 with a second equivalent of trityl cation or of the branched oligosilane 13 with two equivalents of trityl cation, gives at -80 °C the corresponding bissilylium ion 10, an example for a new class of highly reactive poly-Lewis acids.

| S-EPMC9305540 | biostudies-literature

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