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Journals and Conferences
A series of calixarenes substituted with 2-acetamido-2-deoxy-beta-D-glucopyranose linked by a thiourea spacer was prepared and tested for binding activity to heterogeneously expressed activation receptors of the rat natural killer cells NKR-P1, and the receptor CD69 (human NK cells, macrophages). In the case of NKR-P1, the binding affinity of… (More)
S-alkylation of all four thiacalixarene conformations was accomplished using alkyl triflates. The corresponding sulfonium salts are formed in a highly regio- and stereoselective manner depending on the conformation used. Interestingly, only mono- or disubstituted sulfonium salts can be prepared. Although many regio- and stereoisomers are theoretically… (More)
Monohalogenation of thiacalixarene in the cone conformation gave either the meta- or para-substituted isomers depending on the halogen and reaction conditions used. Surprisingly, the same reaction with the 1,3-alternate conformer led only to the meta isomer. This is the first example of such a conformation-dependent regioselectivity in… (More)
We synthesized 25,26,27,28-tetrakis(11-sulfanylundecyloxy)calixarene (CALIX) sensitive to dopamine and confirmed its structure by (1)H NMR and mass spectrometry. Chemisorption of CALIX molecules or their mixtures with 1-dodecanethiols (DDT) or hexadecanethiols (HDT) resulted in formation of compact low permeable monolayers as revealed by cyclic… (More)
[structure: see text] Appending tetraphenylporphyrin units to the calixarene skeleton via the ureido function leads to novel anion receptors designed for anion and/or cation detection by UV-vis spectroscopy. Calixarenes in the cone or 1,3-alternate conformations bearing two ureido moieties on the upper rim represent well-preorganized cavities where the… (More)
The introduction of a 2-pyridylsulfoxide moiety into the upper rim of calixarenes enabled the synthesis of unprecedented derivatives with intramolecularly bridged meta positions of two neighbouring aromatic subunits. Palladium-catalysed double C-H activation thus represents a straightforward way to a completely novel type of calixarenes.
Regioselective derivatization via an organomercury intermediate allowed for the introduction of carboxylic acid functionality into the meta position of the calixarene skeleton. Intramolecular Friedel-Crafts cyclization led to a novel type of calixarene containing a ketone bridging moiety. Subsequent attack of the ketone by organometallic compounds… (More)
To reveal the alternative ways for upper-rim thiacalixarene derivatization, the formylation reactions (Gross and/or Duff conditions) of the corresponding tetrapropoxythiacalixarene immobilized in the 1,3-alternate conformation were systematically studied. Surprisingly, albeit using an excess of the formylation agent, only two formyl groups were… (More)
The meta-iodo derivative, fixed in the cone conformation, enables the gram-scale preparation of a meta-bridged calixarene. This intermediate, possessing a fluorene moiety within the macrocyclic skeleton, can be regioselectively alkylated on the corresponding methylene bridge to form a unique substitution pattern in classical calixarene chemistry.
NMR spectroscopy, X-ray diffraction analysis, and quantum chemical calculations were used for conformational behavior study of partially alkylated thiacalixarenes bearing methyl (1), ethyl (2), or propyl (3) groups at the lower rim. The conformational properties are governed by two basic effects: (i) stabilization by intramolecular hydrogen bonds, and… (More)