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Themed collection In celebration of Julius Rebek’s 75th Birthday

41 items
Editorial

Editorial: In celebration of the 75th birthday of Professor Julius Rebek, Jr.

A special issue dedicated to Professor Julius Rebek, Jr.

Graphical abstract: Editorial: In celebration of the 75th birthday of Professor Julius Rebek, Jr.
Highlight

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.

Graphical abstract: 19F-GEST NMR: studying dynamic interactions in host–guest systems
Open Access Highlight

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.

Graphical abstract: Neglected sulfur(vi) pharmacophores in drug discovery: exploration of novel chemical space by the interplay of drug design and method development
From the themed collection: Recent Open Access Articles
Review Article

Supramolecular ligands for the extraction of lanthanide and actinide ions

A selection of supramolecular ligands designed to extract f-elements.

Graphical abstract: Supramolecular ligands for the extraction of lanthanide and actinide ions
Review Article

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.

Graphical abstract: Diffusion NMR for the characterization, in solution, of supramolecular systems based on calixarenes, resorcinarenes, and other macrocyclic arenes
Review Article

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.

Graphical abstract: Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates
Research Article

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.

Graphical abstract: Hybrid ligands with calixarene and thiodigalactoside groups: galectin binding and cytotoxicity
Research Article

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.

Graphical abstract: An empirical study of amide–heteroarene π-stacking interactions using reversible inhibitors of a bacterial serine hydrolase
Research Article

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.

Graphical abstract: Photocatalytic borylcyclopropanation of α-boryl styrenes
Research Article

Quantification of the hydrophobic effect using water-soluble super aryl-extended calix[4]pyrroles

We report the quantification of the hydrophobic effect using a model system based on water-soluble super aryl-extended calix[4]pyrrole receptors and a series of pyridyl N-oxide derivatives, bearing a non-polar para-substituent, as guests.

Graphical abstract: Quantification of the hydrophobic effect using water-soluble super aryl-extended calix[4]pyrroles
From the themed collection: 2019 Organic Chemistry Frontiers HOT articles
Research Article

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.

Graphical abstract: A pore-expanded supramolecular organic framework and its enrichment of photosensitizers and catalysts for visible-light-induced hydrogen production
From the themed collection: 2019 Organic Chemistry Frontiers HOT articles
Research Article

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.

Graphical abstract: Selective synthesis of N-protected exo-spiro[oxirane-3,2′-tropanes]
Research Article

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.

Graphical abstract: Rotaxane-branched dendrimers with aggregation-induced emission behavior
Research Article

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.

Graphical abstract: A biomimetic strategy for the selective recognition of organophosphates in 100% water: synergies of electrostatic interactions, cavity embedment and metal coordination
Research Article

Functionalisable acyclic cucurbiturils

Functionalised acyclic cucurbiturils can be prepared in a straightforward fashion and provide access to a wide variety of substituted derivatives.

Graphical abstract: Functionalisable acyclic cucurbiturils
Research Article

Tunable enforced cavities inside self-assembled capsules

Controlling and tuning the molecular recognition properties is a crucial task in host–guest chemistry.

Graphical abstract: Tunable enforced cavities inside self-assembled capsules
Research Article

2H NMR reveals liquid state-like dynamics of arene guests inside hexameric pyrogallol[4]arene capsules in the solid state

Guest dynamics inside pyrogallol[4]arene hexamers in the solid state are sensitive to structure external to the host.

Graphical abstract: 2H NMR reveals liquid state-like dynamics of arene guests inside hexameric pyrogallol[4]arene capsules in the solid state
Research Article

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.

Graphical abstract: Using light to control the inhibition of Karstedt's catalyst
Research Article

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.

Graphical abstract: Study of through-space substituent–π interactions using N-phenylimide molecular balances
Research Article

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.

Graphical abstract: Synthesis, photophysical properties, and self-dimerization studies of 2-λ5-phosphaquinolin-2-ones
Research Article

Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene

A ditopic water-soluble resorcinarene is shown to bind salts and undergo self-inclusion to assembly into a supramolecular polymer.

Graphical abstract: Binding properties and supramolecular polymerization of a water-soluble resorcin[4]arene
Research Article

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.

Graphical abstract: Calixarene-based alkynyl-bridged gold(i) isocyanide and phosphine complexes as building motifs for the construction of chemosensors and supramolecular architectures
Research Article

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.

Graphical abstract: Symmetric and nonsymmetric bis-hemithioindigos – precise visible light controlled shape-shifters
Research Article

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.

Graphical abstract: Chiral self-sorting behaviour of [2.2]paracyclophane-based bis(pyridine) ligands
Research Article

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.

Graphical abstract: Supramolecularly assisted synthesis of chiral tripodal imidazolium compounds
Research Article

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.

Graphical abstract: Mechanical generation of isocyanate by mechanically induced retro [2 + 2] cycloaddition of a 1,2-diazetidinone mechanophore
Research Article

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.

Graphical abstract: Synthesis of a sumanenyl hafnocene complex
Research Article

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.

Graphical abstract: Structural and computational characterization of a bridging zwitterionic-amidoxime uranyl complex
Research Article

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.

Graphical abstract: A l-glutamate-responsive delivery system based on enzyme-controlled self-immolative arylboronate-gated nanoparticles
Research Article

Insights into the synthesis of pillar[5]arene and its conversion into pillar[6]arene

The synthesis of pillar[5]arenes from p-dialkoxybenzene and formaldehyde in the presence of iron(III) chloride and tetramethylammonium chloride under mild reaction conditions was investigated in detail.

Graphical abstract: Insights into the synthesis of pillar[5]arene and its conversion into pillar[6]arene
Research Article

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.

Graphical abstract: Guest-mediated chirality transfer in the host–guest complexes of an atropisomeric perylene bisimide cyclophane host
Research Article

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.

Graphical abstract: Dimerization of substituted 4-aryl-1,3-diacetylenes – quantum chemical calculations and kinetic studies
Research Article

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.

Graphical abstract: A new water-soluble cavitand with deeper guest binding properties
Research Article

Temperature-induced large amplitude conformational change in the complex of oxatub[4]arene revealed via rotaxane synthesis

Oxatub[4]arene was revealed via rotaxane synthesis to show a large amplitude conformational response to temperature change.

Graphical abstract: Temperature-induced large amplitude conformational change in the complex of oxatub[4]arene revealed via rotaxane synthesis
Research Article

Synthesis of a [20]phenacene dodeca-ester by controlled condensation of seven naphthalene-based building blocks

A soluble [20]phenacene dodeca-ester has been synthesized by Perkin strategy from naphthalene-based building blocks using complementary protecting techniques.

Graphical abstract: Synthesis of a [20]phenacene dodeca-ester by controlled condensation of seven naphthalene-based building blocks
Research Article

Rotational isomerism of the amide units in rotaxanes based on a cyclic tetraamide and secondary ammonium ions

We describe the synthesis of [2]rotaxanes consisting of a macrocyclic tetraamide and mono- and bis-ammonium ions and their conformational isomerism.

Graphical abstract: Rotational isomerism of the amide units in rotaxanes based on a cyclic tetraamide and secondary ammonium ions
Research Article

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.

Graphical abstract: Supramolecular crowns: a new class of cyclic hydrogen-bonded cavitands
Research Article

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.

Graphical abstract: Amidinium–carboxylate salt bridge mediated proton-coupled electron transfer in a donor–acceptor supramolecular system
Research Article

Red-light-responsive molecular encapsulation in water: an ideal combination of photochemistry and host–guest interaction

Red-light-responsive CB[8]-mediated host–guest system featured with high photoisomerization ratio was fabricated which could be used as molecular container with red-light-activated release ability.

Graphical abstract: Red-light-responsive molecular encapsulation in water: an ideal combination of photochemistry and host–guest interaction
Research Article

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.

Graphical abstract: Encapsulation of dihydrogenphosphate ions as a cyclic dimer to the cavities of site-specifically modified indolocarbazole-pyridine foldamers
Research Article

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.

Graphical abstract: Pyridine-terminated low gap π-conjugated oligomers: design, synthesis, and photophysical response to protonation and metalation
41 items

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.


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