Search results for "calixarene"

Hydrogen-Bonded Analogues of Cavitands

2000

Self-Assembled Hydrogen-Bonded Dimeric Capsules with High Kinetic Stability

2000

Hydrogen bonded calixarene capsules kinetically stable in DMSO.

2002

Half-life times up to 4 days in DMSO at room temperature are observed for the decomposition of dimeric capsules of urea substituted calix[4]arenes held together by a combination of hydrogen bonds, mechanical entanglement and cation–π interactions.

Hydrogen-bonded dimers of a thiacalixarene substituted by carbamoylmethylphosphineoxide groups at the wide rim.

2006

A thiacalix[4]arene derivative bearing four carbamoylmethylphosphineoxide groups at the wide rim forms hydrogen-bonded, dimeric capsules with S8 symmetry in the crystalline state and in apolar solvents, where the inclusion of cationic guests could be proved by 1H NMR and ESI mass spectra.

Tetraurea calix[4]arenes with sulfur functions: synthesis, dimerization to capsules, and self-assembly on gold.

2007

Various calix[4]arene derivatives, fixed in the cone conformation by decylether groups and functionalized at their wide rim by urea residues, were synthesized. In two compounds (4f,g) sulfur functions were attached to the urea groups via different spacers in order to allow binding to metal surfaces. While they exist as single molecules in polar solvents, tetraurea calix[4]arenes of this type (4) combine to form dimeric capsules in aprotic, apolar solvents. A solvent molecule is usually included in such a capsule, if no guest with a higher affinity is present. In the presence of an equimolar amount of the tetratosylurea 5, the exclusive formation of heterodimers, consisting of one molecule o…

Narrow rim CMPO/adamantylcalix[4]arenes for the extraction of lanthanides and actinides

2011

Abstract Six p-(1-adamantyl)calix[4]arenes 7, 8 with four differently attached diphenyl-carbamoylmethylphosphine oxide (CMPO) functions at the narrow rim were synthesized. This series was extended by adamantylcalix[4]arenes with two CMPO and two ester, acid or (diethylphosphono)acetylamino groups. Structures of new compounds were proved by NMR, mass-spectrometry and a single-crystal X-ray analysis for the intermediate di-phthalimide 103. The extraction studies towards selected lanthanides and thorium showed that the ligands 7 surpassed the corresponding p-H, p-tert-butyl and p-tert-octyl analogues 3–5 in lanthanide extraction while thorium was extracted with the same or lesser extent. For t…

tert-Butyl-calix[4]arenes Substituted at the Narrow Rim with Cobalt Bis(dicarbollide)(1–) and CMPO Groups – New and Efficient Extractants for Lanthan…

2007

Calix[4]arene derivatives bearing two residues A(–) derived from cobalt bis(dicarbollide)(1–) (1) and two CMPO groups B at their narrow rim were synthesized from tBu-calix[4]arene in four steps. The first step involved the preparation of tBu-calix[4]arene diether derivatives with appropriate precursors for amino groups (mostly nitriles 3). These were O-alkylated through ring-opening reactions with the zwitterionic dioxane derivative [(8-O(CH2CH2)2O-1,2-C2B9H10)-(1′,2′-C2B9H11)-3,3′-Co]0 (10) to produce ionic nitrile derivatives 4. Reduction of the nitrile groups with BH3·SMe2 (or deprotection in the case of the corresponding phthalimido or Boc derivatives 8) led to a series of diamines 5a–f…

Lanthanide complexation with CMPO and CMPO-calix[4]arenes in solution: spectrophotometric and electrospray mass spectrometric approaches.

2007

The binding of lanthanide(III) cations with organophosphorous ligands like CMPO and related calix[4]arene-based derivatives have been investigated using two experimental methods. The stability constants of the lanthanum, europium and ytterbium complexes were first determined in methanol by UV absorption spectrophotometry in the presence of nitrate or chloride anions. The results showed that the stoichiometry and the stability of the complexes formed depend on the position of the CMPO moieties either on the wide or the narrow rim of the calixarene scaffold, the nature of the medium, the conformational mobility of the ligands. Complexation of lanthanum was also followed by ESI-mass spectromet…

Tetra-CMPO-derivatives of calix[4]arenes fixed in the 1,3-alternate conformation

2010

Calix[4]arene derivatives fixed in the 1,3-alternate conformation and substituted at one side by four carbamoylmethylphosphine oxide (CMPO) residues were synthesised. Two CMPO groups are directly attached to the wide rim, while the second pair is bound to the narrow rim via a tri- or tetramethylene spacer. Similar compounds, in which two CMPO groups at the wide rim are combined with two picolinamide groups or two ionisable carboxylic groups at the narrow rim, were also prepared. Some of these calixarene derivatives were studied as extractants for lanthanides (La3+, Eu3+, Yb3+) and thorium (Th4+) from acidic solution into methylene chloride. For selected samples, stability constants in metha…

Conformationally Mobile Wide Rim Carbamoylmethylphosphine Oxide (CMPO)-Calixarenes

1999

Six new calix[4]arene derivatives 2a–f have been synthesised, bearing CMPO-like functions (-NH–C(O)–CH2–P(O)Ph2) at their wide rim. They differ by their alkoxy groups at the narrow rim, comprising all possible combinations of methoxy and syn-propoxy groups including the conformationally mobile tetramethyl ether 2e and the tetrapropyl ether 2f fixed in the cone conformation. Their extraction behaviour for thorium(IV) and several lanthanides(III) from 1M HNO3 to dichloromethane has been studied and compared also to non cyclic calixarene analogues 6a–e. Surprisingly the best extraction results were found for the 1,2-dimethoxy-3,4-dipropoxy derivative 2c among the calixarenes and for the tetram…