- Building Covalent Molecular Capsules by Thiol-Michael Addition Click Reaction
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The thiol-Michael addition (TMA) is a powerful methodology to click several fragments together, despite having been underestimated in the synthesis of complex systems for supramolecular chemistry. Herein, a very fast and efficient method has been developed to make covalent molecular capsules by taking advantage of the TMA click reaction. Several scaffolds commonly used in supramolecular chemistry, such as calixarenes, CTV, or cavitands, have been used to quickly obtain covalent cages. Additionally, a 'click&click' procedure has been also developed, by sequential combination of TMA and CuAAC click reaction, as an easy and quick way to build complex molecular structures.
- Perretti, Marcelle D.,Pérez-Márquez, Lidia A.,García-Rodríguez, Raúl,Carrillo, Romen
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Read Online
- Supramolecular Alloys from Fluorinated Hybrid Tri4Di6 Imine Cages
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To create innovative materials, efficient control and engineering of pore sizes and their characteristics, crystallinity and stability is required. Eight hybrid Tri4Di6 imine cages with a tunable degree of fluorination and one fully fluorinated Tri4Di6 imine cage are investigated. Although the fluorinated and the non-fluorinated building blocks used herein differ vastly in reactivity, it was possible to gain control over the outcome of the self-assembly process, by carefully controlling the feed ratio. This represents the first hybrid material based on fluorinated/hydrogenated porous organic cages (POCs). These cages with unlimited miscibility in the solid state were obtained as highly crystalline samples after recrystallization and even showed retention of the crystal lattice, forming alloys. All mixtures and the fully fluorinated Tri4Di6 imine cage were analyzed by MALDI-MS, single-crystal XRD, powder XRD and in regard to thermal stability (TGA).
- Kunde, Tom,Pausch, Tobias,Schmidt, Bernd M.
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supporting information
p. 8457 - 8460
(2021/05/24)
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- Electroactive anion receptor with high affinity for arsenate
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Herein, we present the synthesis and characterization of a macrocyclic polyamide cage that incorporates redox-active 1,4-dithiin units. UV/vis titration experiments with eight anions in acetonitrile revealed high affinity for H2AsO4
- Etkind, Samuel I.,Vander Griend, Douglas A.,Swager, Timothy M.
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supporting information
p. 10050 - 10061
(2020/10/02)
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- MACROCYCLIC COMPOUNDS
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The present invention relates to macrocyclic compounds which are capable of selective binding to a target saccharide (e.g. glucose), making them particularly well suited for use in saccharide sensing applications. The present invention also relates to processes for the preparation of said compounds, to compositions and devices comprising them, and to their use in the detection of a target saccharide.
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Paragraph 00218
(2018/10/19)
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- Alkane oxidation catalysed by a self-folded multi-iron complex
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A preorganised ligand scaffold is capable of coordinating multiple Fe(II) centres to form an electrophilic CH oxidation catalyst. This catalyst oxidises unactivated hydrocarbons including simple, linear alkanes under mild conditions in good yields with selectivity for the oxidation of secondary CH bonds. Control complexes containing a single metal centre are incapable of oxidising unstrained linear hydrocarbons, indicating that participation of multiple centres aids the CH oxidation of challenging substrates.
- Mettry, Magi,Moehlig, Melissa Padilla,Gill, Adam D.,Hooley, Richard J.
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p. 120 - 128
(2016/11/09)
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- Enhanced fluorescence of silver nanoclusters stabilized with branched oligonucleotides
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DNA stabilized silver nanoclusters (AgNCs) are promising optical materials, whose fluorescence properties can be tuned by the selection of the DNA sequence employed. In this work we have used modified oligonucleotides in the preparation of AgNCs. The fluorescent intensity obtained was 60 times higher than that achieved with standard oligonucleotides. The Royal Society of Chemistry.
- Latorre, Alfonso,Lorca, Romina,Zamora, Felix,Somoza, Alvaro
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supporting information
p. 4950 - 4952
(2013/06/26)
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- Synthesis and coordination chemistry of a tris(benzene-o-dithiolato)- functionalized ligand as a siderophore analog
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As a siderophore analog, the tripodal tris(benzene-o-dithiol)- functionalized ligand H6-5, has been synthesized in four steps including the reaction of 1,3,5-(triaminomethyl)-2,4,6-triethylbenzene and 2,3-bis(isopropylmercapto)benzoyl chloride followed by removal of the S-protecting groups. Reaction of compound H6-5 with [Ti(OPr) 4] in the presence of (NEt4)Cl leads to the formation of complex (NEt4)2[Ti(5)] featuring three bidentate benzene-o-dithiolato donors from one ligand coordinated to the metal center. An X-ray diffraction structure analysis with crystals of (NEt4) 2[Ti(5)]·DMF has shown that the coordination geometry at the metal center is best described as distorted trigonal-prismatic with a twist angle of φav = 18:5°.
- Ruppel, Susanne,Schulte To Brinke, Christian,Hahn, F. Ekkehardt
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p. 551 - 556
(2013/07/26)
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- Differential recognition of mannose-based polysaccharides by tripodal receptors based on a triethylbenzene scaffold substituted with trihydroxybenzoyl moieties
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The tripodal receptors 1 and 2 based on a triethylbenzene scaffold substituted with trihydroxybenzoyl groups have been synthesised. The conformational preferences and carbohydrate-binding ability of 1 and 2 have been examined by NMR spectroscopy and model
- Carrero, Paula,Arda, Ana,Alvarez, Monica,Doyagueez, Elisa G.,Rivero-Buceta, Eva,Quesada, Ernesto,Prieto, Alicia,Solis, Dolores,Camarasa, Maria Jose,Perez-Perez, Maria Jesus,Jimenez-Barbero, Jesus,San-Felix, Ana
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- C3-symmetric proline-functionalized organocatalysts: Enantioselective michael addition reactions
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C3-Symmetric, tripodal catalyst 4 based on 1,3,5- triethylbenzene, which incorporates the features of a molecular receptor, is shown to catalyze Michael addition reactions ofcarbonyl compounds to β-nitrostyrenes in a high stereoselectivity (up to 99:1a dr and up to 98%ee). Copyright
- Moorthy, Jarugu Narasimha,Saha, Satyajit
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supporting information; experimental part
p. 6359 - 6365
(2011/03/17)
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- Solvent-induced amphiphilic molecular baskets: Unimolecular reversed micelles with different size, shape, and flexibility
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Amphiphilic molecular baskets were obtained by attaching facially amphiphilic cholate groups to a covalent scaffold (calix[4]arene or 1,3,5-2,4,6-hexasubstituted benzene). In a solvent mixture consisting of mostly a nonpolar solvent (i.e., CCl4
- Ryu, Eui-Hyun,Yan, Jie,Zhong, Zhenqi,Zhao, Yan
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p. 7205 - 7213
(2008/02/01)
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- Preparation of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene from two versatile 1,3,5-tri(halosubstituted) 2,4,6-triethylbenzene derivatives
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The use of 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene and the intermediates 1,3,5-tris(halomethyl)-2,4,6-triethylbenzene (halo = bromo and chloro) compounds, have been utilized as scaffolds for many molecular receptors. We report here for the first time a detailed practical synthetic procedure, starting from benzene, and in four straightforward steps, to prepare 1,3,5-tris(aminomethyl)-2,4,6-triethylbenzene, a very versatile molecular scaffold. The added advantage is the limited chromatography in the purification procedure. Georg Thieme Verlag Stuttgart.
- Wallace, Karl J.,Hanes, Robert,Anslyn, Eric,Morey, Jeroni,Kilway, Kathleen V.,Siegel, Jay
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p. 2080 - 2083
(2007/10/03)
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- Disposable receptor-based optical sensor for nitrate
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A new optical absorption-based disposable sensor for nitrate is described. The nitrate-sensitive element is a bicyclic cyclophane receptor next to a suitable pH-sensitive lipophilic dye immobilized in a plasticized polymeric membrane. The rigid amide-base
- Capitan-Vallvey, Luis Fermin,Arroyo-Guerrero, Eduardo,Fernandez-Ramos, Maria Dolores,Santoyo-Gonzalez
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p. 4459 - 4466
(2008/02/02)
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- Metal triggered fluorescence sensing of citrate using a synthetic receptor
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A metal containing fluorescent chemosensor was designed, synthesized, and studied for the quantification of citrate in common beverages. The sensor consists of Cu(II) bound by a 1,10-phenanthroline ligand which is attached to a bis(aminoimidazolium) recep
- Cabell, Larry A.
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p. 315 - 323
(2007/10/03)
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- "Flexiball" toolkit: A modular approach to self-assembling capsules
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We report the synthesis and characterization of new, self-assembling molecular capsules. The modular strategy makes use of glycoluril building blocks available in multigram amounts combined with aromatic spacer elements. The lengthy syntheses encountered with earlier generations of capsules are avoided, and several capsules of nanometer dimensions are now accessible. Single bond attachments between spacers and glycoluril modules result in monomers as dimeric capsules that are less rigid than their earlier counterparts. The host-guest properties of the homo- and heterodimeric capsules were studied using a combination of NMR and ESI-mass spectrometry. They show a less pronounced selectivity for guests of different sizes, and their increased flexibility prevents self-assembly when no rigidifying elements are present on the central spacer unit. Some of the new capsules bear inwardly directed, secondary amide N-H protons. These can be further functionalized, as shown by their methylation to give tertiary analogues. The structures hold broader implications for the placement of functional groups on concave molecular surfaces.
- O'Leary,Szabo,Svenstrup,Schalley,Luetzen,Schaefer,Rebek Jr.
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p. 11519 - 11533
(2007/10/03)
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- Control of functional group proximity and direction by conformational networks: Synthesis and stereodynamics of persubstituted arenes
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The cooperative nonbonded interactions present in hexaethylbenzene result in an arrangement of alkyl groups such that the 1,3,5 and 2,4,6 substituents point to opposite faces of the benzene ring. Correspondingly, derivatives of hexaethylbenzene have their functional groups convergent (meta as in 1,3,5-trisubstituted-2,4,6-triethylbenzene) or divergent (ortho, para as in 1,2-disubstituted-3,4,5,6-tetraethylbenzenes or 1,4-disubstituted-2,3,5,6-tetraethylbenzenes) due to this cooperative conformational network. To illustrate this structural feature and probe its dynamics, 1,4-di-X-2,3,5,6-tetraethylbenzenes have been synthesized. The dynamic stereochemistry of the disubstituted compounds has been studied by variable temperature 1H NMR spectroscopy. Using the same strategy, the 1,3,5-tris(CH2Y)-2,4,6-triethylbenzenes have also been prepared. The steric bulk of the substituent in the disubstituted compounds has been found to influence the barrier height. The trends found are applicable for the use of these compounds as angular building blocks for the design of ligands, polymers, and supramolecular architectures.
- Kilway, Kathleen V,Siegel, Jay S
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p. 3615 - 3627
(2007/10/03)
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- Azacalixarene: Synthesis, conformational analysis, and recognition behavior toward anions
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The synthesis of an azacalix[4]arene (4) having four primary amino groups on the upper rim has been achieved. The synthesis was accomplished by a one-step cyclization starting from two easily synthesized building blocks. 1H NMR spectra indicate
- Niikura, Kenichi,Anslyn, Eric V.
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p. 2769 - 2775
(2007/10/03)
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- A synthetic receptor selective for citrate
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Applied molecular recognition strong and selective binding of citrate in highly competitive media such as water and orange juice is reported. Five steps are enough to synthesize receptor 1 that is complementary in charge and shape to citrate. Electrostati
- Metzger,Lynch,Anslyn
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p. 862 - 865
(2007/10/03)
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