Editorial: In celebration of the 75th birthday of Professor Julius Rebek, Jr.
A special issue dedicated to Professor Julius Rebek, Jr.
19F-GEST NMR: studying dynamic interactions in host–guest systems
GEST NMR provides dynamic information on host–guest systems. It allows signal amplification of low concentrated complexes, detection of intermolecular interactions and quantification of guest exchange rates.
Neglected sulfur(VI) pharmacophores in drug discovery: exploration of novel chemical space by the interplay of drug design and method development
The key learnings of the utilization of sulfoximines, sulfondiimines and sulfonimidamides in drug discovery at Bayer AG are shared.
Supramolecular ligands for the extraction of lanthanide and actinide ions
A selection of supramolecular ligands designed to extract f-elements.
Diffusion NMR for the characterization, in solution, of supramolecular systems based on calixarenes, resorcinarenes, and other macrocyclic arenes
The use of diffusion NMR in studying calixarenes and other arene-based supramolecular systems is described, emphasizing the pivotal role played by the calixarene community in transforming the methods into a routine tool used in supramolecular chemistry.
Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates
This review reports a comprehensive compilation of gold-catalyzed heterocyclic synthesis by using α-imino gold carbene complexes as the proposed intermediates.
Hybrid ligands with calixarene and thiodigalactoside groups: galectin binding and cytotoxicity
Galectins have diverse functions and are involved in many biological processes because of their complex intra- and extracellular activities.
An empirical study of amide–heteroarene π-stacking interactions using reversible inhibitors of a bacterial serine hydrolase
The binding of diverse heterocyclic probe ligands to a bacterial hydrolase reveals important features of amide–heteroarene π-stacking interactions.
Photocatalytic borylcyclopropanation of α-boryl styrenes
A diastereoselective borylcyclopropanation of α-MIDA-boryl styrenes is developed using 4CzIPN as a catalyst under visible-light irradiation. The scope of this photocatalytic method is explored, and the utility of the resulting doubly borylated cyclopropanes is demonstrated by the selective transformations of one of the two boryl groups.
Quantification of the hydrophobic effect using water-soluble super aryl-extended calixpyrroles
We report the quantification of the hydrophobic effect using a model system based on water-soluble super aryl-extended calixpyrrole receptors and a series of pyridyl N-oxide derivatives, bearing a non-polar para-substituent, as guests.
A pore-expanded supramolecular organic framework and its enrichment of photosensitizers and catalysts for visible-light-induced hydrogen production
A 3.6 nm-pore SOF is constructed, which adsorbs both photosensitizers and polyoxometallates for visible light-induced proton reduction to produce H2.
Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]
N-Cbz- and N-Boc-protected exo-spiro[oxirane-3,2′-tropanes] were selectively synthesized via either epoxidation or hydroxybromination/dehydrobromination of the corresponding alkenes.
Rotaxane-branched dendrimers with aggregation-induced emission behavior
By introducing a 9,10-distyrylanthrance (DSA) moiety as the core, we demonstrated the synthesis of a new family of rotaxane-branched dendrimers G1–G3 through the controllable divergent approach.
A biomimetic strategy for the selective recognition of organophosphates in 100% water: synergies of electrostatic interactions, cavity embedment and metal coordination
A biomimetic receptor allows selective recognition of organophosphates in water thanks to multipoint recognition associating coordination, electrostatics and cavity hosting.
Functionalisable acyclic cucurbiturils
Functionalised acyclic cucurbiturils can be prepared in a straightforward fashion and provide access to a wide variety of substituted derivatives.
Tunable enforced cavities inside self-assembled capsules
Controlling and tuning the molecular recognition properties is a crucial task in host–guest chemistry.
2H NMR reveals liquid state-like dynamics of arene guests inside hexameric pyrogallolarene capsules in the solid state
Guest dynamics inside pyrogallolarene hexamers in the solid state are sensitive to structure external to the host.
Using light to control the inhibition of Karstedt's catalyst
Light is used to control a ligand that acts as an inhibitor for a metal-based catalyst.
Study of through-space substituent–π interactions using N-phenylimide molecular balances
Substituent–π interactions associated with aromatic stacking interactions were experimentally measured using a small N-phenylimide molecular balance model system.
Synthesis, photophysical properties, and self-dimerization studies of 2-λ5-phosphaquinolin-2-ones
Rationally designed phosphaquinolinone derivatives containing electron-donating and/or -withdrawing groups are reported, with dimerization constants up to 525 M−1.
Binding properties and supramolecular polymerization of a water-soluble resorcinarene
A ditopic water-soluble resorcinarene is shown to bind salts and undergo self-inclusion to assembly into a supramolecular polymer.
Calixarene-based alkynyl-bridged gold(I) isocyanide and phosphine complexes as building motifs for the construction of chemosensors and supramolecular architectures
A calixarene-based alkynyl-bridged Au(I) isocyanide complex with a triazolyl group as a receptor site has been synthesized and demonstrated to be a selective chemosensor for Zn2+ based on Au(I)⋯Au(I) interactions.
Symmetric and nonsymmetric bis-hemithioindigos – precise visible light controlled shape-shifters
A series of bis-hemithioindigo photoswitches with different molecular setups are presented allowing precise manipulation of molecular shapes with visible light.
Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine) ligands
[2.2]Paracyclophane-based bis(pyridine) ligands form dinuclear complexes upon coordination to palladium(II) ions, however, with distinct differences concerning their chiral self-sorting ability.
Supramolecularly assisted synthesis of chiral tripodal imidazolium compounds
Supramolecular interactions based on amide groups direct the preferential formation of tritopic instead of monotopic or ditopic imidazolium compounds.
Mechanical generation of isocyanate by mechanically induced retro [2 + 2] cycloaddition of a 1,2-diazetidinone mechanophore
Mechanical activation of a 1,2-diazetidinone mechanophore via ultrasonic sonication leads to the formation of isocyanate and imine products.
Synthesis of a sumanenyl hafnocene complex
A convex-bound sumanenyl hafnocene complex was selectively synthesized, and the catalytic activity of sumanenyl metallocenes was demonstrated in the carboalumination reaction.
Structural and computational characterization of a bridging zwitterionic-amidoxime uranyl complex
A bridging (μ2) neutral zwitterionic amidoxime binding mode previously unobserved between amidoximes and uranyl is reported and compared to other uranyl amidoxime complexes.
A L-glutamate-responsive delivery system based on enzyme-controlled self-immolative arylboronate-gated nanoparticles
Janus Au–mesoporous silica nanoparticles functionalized with L-glutamate oxidase and self-immolative arylboronate as a L-glutamate-responsive delivery system.
Insights into the synthesis of pillararene and its conversion into pillararene
The synthesis of pillararenes from p-dialkoxybenzene and formaldehyde in the presence of iron(III) chloride and tetramethylammonium chloride under mild reaction conditions was investigated in detail.
Guest-mediated chirality transfer in the host–guest complexes of an atropisomeric perylene bisimide cyclophane host
Chirality transfer upon preferential binding of homochiral guests to one stereoisomer of a conformationally equilibrated atropisomeric cyclophane is reported.
Dimerization of substituted 4-aryl-1,3-diacetylenes – quantum chemical calculations and kinetic studies
Thermal dimerization of 4-aryl-1,3-diacetylenes resulting in diradical intermediates were investigated by experimental and quantum chemical studies.
A new water-soluble cavitand with deeper guest binding properties
A new water-soluble cavitand captured hydrophobic or amphiphilic molecules in an aqueous solution owing to its deep aromatic pocket.
Temperature-induced large amplitude conformational change in the complex of oxatubarene revealed via rotaxane synthesis
Oxatubarene was revealed via rotaxane synthesis to show a large amplitude conformational response to temperature change.
Synthesis of a phenacene dodeca-ester by controlled condensation of seven naphthalene-based building blocks
A soluble phenacene dodeca-ester has been synthesized by Perkin strategy from naphthalene-based building blocks using complementary protecting techniques.
Rotational isomerism of the amide units in rotaxanes based on a cyclic tetraamide and secondary ammonium ions
We describe the synthesis of rotaxanes consisting of a macrocyclic tetraamide and mono- and bis-ammonium ions and their conformational isomerism.
Supramolecular crowns: a new class of cyclic hydrogen-bonded cavitands
A novel design of highly preorganized bicyclic monomers, based on quadruple hydrogen bonding motifs, is proposed to access noncovalent cavitands with large internal volumes and interesting shapes.
Amidinium–carboxylate salt bridge mediated proton-coupled electron transfer in a donor–acceptor supramolecular system
A supramolecular polymer that allows for intrapolymer proton-coupled photoinduced electron transfer was constructed by means of amidinium-carboxylate salt bridges.
Red-light-responsive molecular encapsulation in water: an ideal combination of photochemistry and host–guest interaction
Red-light-responsive CB-mediated host–guest system featured with high photoisomerization ratio was fabricated which could be used as molecular container with red-light-activated release ability.
Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the cavities of site-specifically modified indolocarbazole-pyridine foldamers
Site-specifically modified aromatic foldamers can encapsulate dihydrogen phosphate ions as a cyclic dimer via the formation of twelve hydrogen bonds.
Pyridine-terminated low gap π-conjugated oligomers: design, synthesis, and photophysical response to protonation and metalation
Pyridine terminated donor–acceptor π-conjugated oligomers have been prepared and their absorption and emission properties have been evaluated with respect to protonation and metalation.
About this collection
This themed collection published from Organic Chemistry Frontiers celebrates the 75th Birthday of Professor Julius Rebek in 2019!
Professor Julius Rebek, Jr. (Skaggs & Skripps Research Institutes) is an internationally recognized leader in bioorganic and supramolecular chemistry who pioneered the fields of hydrogen-bonded cleft receptors, synthetic self-replication and self-assembled molecular capsules.
Guest Editors Pablo Ballester (ICIQ Institute of Chemical Research of Catalonia) and Frank Würthner (University of Würzburg) welcome contributions from Professor Rebek’s friends and colleagues to this collection.
More articles will be added as soon as they are published.