Themed collection Macrocycle-based Supramolecular Elements

45 items
Editorial

Macrocycle-based supramolecular elements

Hai-Bo Yang and Christoph A. Schalley introduce this themed issue on macrocyle-based supramolecular elements.

Graphical abstract: Macrocycle-based supramolecular elements
From the themed collection: Macrocycle-based Supramolecular Elements
Highlight

Macrocyclic and acyclic supramolecular elements for co-precipitation of square-planar gold(III) tetrahalide complexes

Non-covalent interactions control the solid-state packing of AuX4 anions (yellow circles) co-precipitated with different supramolecular elements.

Graphical abstract: Macrocyclic and acyclic supramolecular elements for co-precipitation of square-planar gold(iii) tetrahalide complexes
Open Access Review Article

Direct synthetic routes to functionalised crown ethers

Modification of crown ethers via grafting of functional groups represents a convenient yet underexplored tool.

Graphical abstract: Direct synthetic routes to functionalised crown ethers
Open Access Research Article

Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers

Polycyclic aromatic hydrocarbon chromophores that show an ideal bipartition between fluorescence and singlet oxygen production have been developed.

Graphical abstract: Bis-borylated arylisoquinoline-derived dyes with a central aromatic core: towards efficient fluorescent singlet-oxygen photosensitizers
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Customized self-assembled molecules: rim adjustable coronal polygons with multiple-folds symmetry

Three desired discrete metallomacrocyclic wreaths with four-, five- and six-fold symmetry were successfully realized in a controlled fashion.

Graphical abstract: Customized self-assembled molecules: rim adjustable coronal polygons with multiple-folds symmetry
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Divergent synthesis of pyrrolidine and glutamic acid derivatives using a macrocyclic phase-transfer catalyst under high-pressure conditions

The reactivity of the glycine ketimine ester with α,β-unsaturated ketones in the presence of macrocyclic hybrid phase-transfer catalysts under high pressure conditions has been investigated.

Graphical abstract: Divergent synthesis of pyrrolidine and glutamic acid derivatives using a macrocyclic phase-transfer catalyst under high-pressure conditions
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Allosteric binding of sodium deoxycholate by a bis(β-cyclodextrin)-2,2′-bipyridine receptor

The allosteric effect of a new bis(β-cyclodextrin) receptor amounts to a more than 18-fold increase of its binding affinity towards sodium deoxycholate upon addition of a zinc(II) phenanthroline complex as an effector.

Graphical abstract: Allosteric binding of sodium deoxycholate by a bis(β-cyclodextrin)-2,2′-bipyridine receptor
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Naphthobox: a selective molecular box for planar aromatic cations

A molecular box with an electron-rich cavity, namely naphthobox, was contructed and showed selective binding to planar aromatic cations.

Graphical abstract: Naphthobox: a selective molecular box for planar aromatic cations
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

A supramolecular dual-donor artificial light-harvesting system with efficient visible light-harvesting capacity

A supramolecular dual-donor artificial light-harvesting system with efficient visible light-harvesting capacity was constructed through the hierarchical self-assembly approach.

Graphical abstract: A supramolecular dual-donor artificial light-harvesting system with efficient visible light-harvesting capacity
From the themed collection: 2021 Organic Chemistry Frontiers HOT articles
Research Article

Switchable supramolecular ensemble for anion binding with ditopic hydrogen-bonded macrocycles

A novel supramolecular strategy has been proposed by using a ditopic H-bonded amide macrocycle that is capable of controlling the binding process in response to external stimulus due to its assembly-and-disassembly-induced anion binding.

Graphical abstract: Switchable supramolecular ensemble for anion binding with ditopic hydrogen-bonded macrocycles
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Efficient one-pot synthesis of [3]catenanes based on Pt(II) metallacycles with a flexible building block

Three [3]catenanes were fabricated in high efficiency through the self-assembly of a 90° platinum(II) receptor, a flexible bis(4,4′-bipyridinium) donor and a crown ether (DB24C8 or DB30C10).

Graphical abstract: Efficient one-pot synthesis of [3]catenanes based on Pt(ii) metallacycles with a flexible building block
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Imino-thiolate-templated synthesis of a chloride-selective neutral macrocyclic host with a specific “turn-off–on” fluorescence response for hypochlorite (ClO)

A precise replacement of one oxygen atom with sulfur allowed a novel thioimidate anion-templated macrocyclization to form a crowded host 2 with the ability to act as a highly selective and sensitive fluorescence probe for hypochlorite (ClO).

Graphical abstract: Imino-thiolate-templated synthesis of a chloride-selective neutral macrocyclic host with a specific “turn-off–on” fluorescence response for hypochlorite (ClO−)
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Synthesis, structure elucidation and functionalization of sulfonamide [2]catenanes

A pyrene-functionalized [2]catenane with switchable optical output was constructed through a novel sulfonamide [2]catenane synthesized by a self-templation approach.

Graphical abstract: Synthesis, structure elucidation and functionalization of sulfonamide [2]catenanes
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Expanded all-phenylene molecular spoked wheels: cutouts of graphenylene-3

All-phenylene molecular spoked wheels, cutouts of graphenylene-3, have been synthesized by intramolecular Yamamoto coupling of the respective dodecabromides.

Graphical abstract: Expanded all-phenylene molecular spoked wheels: cutouts of graphenylene-3
From the themed collection: 2021 Organic Chemistry Frontiers HOT articles
Research Article

Chiral supramolecular polymerization of dicyanostilbenes with emergent circularly polarized luminescence behavior

A novel type of circularly polarized luminescence (CPL) active systems have been constructed via chiral supramolecular polymerization of dicyanostilbene-based monomers.

Graphical abstract: Chiral supramolecular polymerization of dicyanostilbenes with emergent circularly polarized luminescence behavior
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

A multi-responsive supramolecular heparin-based biohybrid metallogel constructed by controlled self-assembly based on metal–ligand, host–guest and electrostatic interactions

A new family of supramolecular heparin-based biohybrid metallogels with multiple stimuli-responsive behaviours was constructed through the controlled self-assembly based on three orthogonal interactions within a single system.

Graphical abstract: A multi-responsive supramolecular heparin-based biohybrid metallogel constructed by controlled self-assembly based on metal–ligand, host–guest and electrostatic interactions
From the themed collection: 2021 Organic Chemistry Frontiers HOT articles
Research Article

Truxene-based covalent organic polyhedrons constructed through alkyne metathesis

Dynamic alkyne metathesis has successfully been employed toward the synthesis of a truxene-based shape-persistent covalent organic polyhedron (COP) with high binding affinity for fullerenes.

Graphical abstract: Truxene-based covalent organic polyhedrons constructed through alkyne metathesis
From the themed collection: 2021 Organic Chemistry Frontiers HOT articles
Research Article

Aryl carbazole-based macrocycles: synthesis, their remarkably stable radical cations and host–guest complexation with fullerenes

Herein, we have designed and synthesized a series of aryl carbazole-based macrocycles and their stable radical cation species and interesting fullerene recognition were systematically investigated.

Graphical abstract: Aryl carbazole-based macrocycles: synthesis, their remarkably stable radical cations and host–guest complexation with fullerenes
From the themed collection: Macrocycle-based Supramolecular Elements
Open Access Research Article

Functional group introduction and aromatic unit variation in a set of π-conjugated macrocycles: revealing the central role of local and global aromaticity

Insights into how the optoelectronic properties of π-conjugated macrocycles evolve as a result of systematic structural changes are presented, helping to develop structure–property relationships and molecular design guidelines.

Graphical abstract: Functional group introduction and aromatic unit variation in a set of π-conjugated macrocycles: revealing the central role of local and global aromaticity
Open Access Research Article

Aqueous assembly of a (pseudo)rotaxane with a donor–π–acceptor axis formed by a Knoevenagel condensation

The incorporation of a linear D–π–A “push–pull” chromophore synthesized by a Knoevenagel condensation as axle of a rotaxane is reported.

Graphical abstract: Aqueous assembly of a (pseudo)rotaxane with a donor–π–acceptor axis formed by a Knoevenagel condensation
Research Article

Perylene bisimide cyclophanes as receptors for planar transition structures – catalysis of stereoinversions by shape-complementarity and noncovalent π–π interactions

Perylene bisimide cyclophanes, ideal receptors for planar aromatic compounds, act as π–π catalysts by stabilizing shape-complementary stereoinversion transition structures.

Graphical abstract: Perylene bisimide cyclophanes as receptors for planar transition structures – catalysis of stereoinversions by shape-complementarity and noncovalent π–π interactions
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Site-selective binding of terpenoids within a confined space of metal–macrocycle framework: substrate-specific promotion or inhibition of cyclization reactions

Terpenoids, (S)-citronellal, nerol, geraniol and farnesol, were site-selectively adsorbed to binding pockets on the pore surface of a metal-macrocycle framework, and their cyclization reaction was controlled in a confined nanospace.

Graphical abstract: Site-selective binding of terpenoids within a confined space of metal–macrocycle framework: substrate-specific promotion or inhibition of cyclization reactions
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Straightforward supramolecular purification of C84 from a fullerene extract

An efficient, one-step protocol for the enrichment of C84 (up to 86%) directly from a fullerene extract is reported, by utilizing a tetragonal prismatic nanocapsule with a suitable size and shape for selective encapsulation.

Graphical abstract: Straightforward supramolecular purification of C84 from a fullerene extract
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Triazolate-based pillarplexes: shape-adaptive metallocavitands via rim modification of macrocyclic ligands

Rim-modified pillarplexes are prepared by a macrocycle-templated synthesis strategy. They exhibit a shape-adaptive behaviour and complementary H-bonding, showing that rim modification can modulate the flexibility and functionality of the cavitand.

Graphical abstract: Triazolate-based pillarplexes: shape-adaptive metallocavitands via rim modification of macrocyclic ligands
From the themed collection: Macrocycle-based Supramolecular Elements
Open Access Research Article

Cucurbitimines – imine cages with concave walls

Kinked tetraaldehyde building blocks lead in condensation reactions with diamines to pumpkin shaped cages – the cucurbitimines.

Graphical abstract: Cucurbitimines – imine cages with concave walls
Research Article

Coordination-driven assembly of actinide-organic polyrotaxanes involving crown ether macrocycles

Using macrocyclic DB24C8 as a new kind of host molecule for a pseudorotaxane ligand, actinide-linked crown ether-based coordination polyrotaxanes, UCER-1 and UCER-2, that are linked by two different uranyl nodes, have been synthesised for the first time.

Graphical abstract: Coordination-driven assembly of actinide-organic polyrotaxanes involving crown ether macrocycles
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Self-division of 2-D sheets in aromatic macrocycle assembly

2-D Sheets from macrocycle assembly undergoes reversible lengthwise division in response to temperature change.

Graphical abstract: Self-division of 2-D sheets in aromatic macrocycle assembly
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Pillar[5]arene-based ion-pair recognition for constructing a [2]pseudorotaxane with supramolecular interaction induced LCST behavior

Here, we report a novel [2]pseudorotaxane based on perbromoethylated pillar[5]arene/imidazolium iodide ionic liquid ion-pair recognition and this pseudorotaxane shows supramolecular interaction induced LCST behavior in solution.

Graphical abstract: Pillar[5]arene-based ion-pair recognition for constructing a [2]pseudorotaxane with supramolecular interaction induced LCST behavior
From the themed collection: Macrocycle-based Supramolecular Elements
Open Access Research Article

Dual-stimuli pseudorotaxane switches under kinetic control

Dual-stimuli pseudorotaxane switches: Threaded complexes dissociate upon deprotonation or oxidation. A mechanical bond changes the influence of a ‘speed bump’ on the outcome of a switching event.

Graphical abstract: Dual-stimuli pseudorotaxane switches under kinetic control
Research Article

Clover leaf-shaped supramolecules assembled using a predesigned metallo-organic ligand

A series of clover-like supramolecular structures were designed and synthesized using a combination of Ru–Zn, Ru–Co, Ru–Mn or Ru–Ni metal ions. These structures with distinct redox properties may have further applications as functional materials.

Graphical abstract: Clover leaf-shaped supramolecules assembled using a predesigned metallo-organic ligand
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Self-assembled luminescent Cu(I) tetranuclear metallacycles based on 3,3′-bipyridine ligands

Three luminescent tetranuclear macrocycles are obtained selectively, applying coordination-driven supramolecular processes to the reaction of 3,3′-bipyridine ligand with in situ formed Cu(I) bimetallic units bearing a coordination angle of ca. 120°.

Graphical abstract: Self-assembled luminescent Cu(i) tetranuclear metallacycles based on 3,3′-bipyridine ligands
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Supramolecular fluorescence sensing of L-proline and L-pipecolic acid

Fluorescent mono-phosphonate calix[4]pyrrole cavitands display selectivity in amino acids' sensing.

Graphical abstract: Supramolecular fluorescence sensing of l-proline and l-pipecolic acid
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Selective formation of spiroborate-based double-stranded hetero-helicates assisted by donor–acceptor interactions

A novel spiroborate-based double-stranded hetero-helicate is selectively formed through donor–acceptor interactions between the central electron-rich porphyrin and electron-deficient naphthalene diimide units.

Graphical abstract: Selective formation of spiroborate-based double-stranded hetero-helicates assisted by donor–acceptor interactions
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Dinuclear helicate or mononuclear pincer lanthanide complexes from one ligand: stereo-controlled assembly and catalysis

By varying the metal/ligand ratio, either dinuclear triple helicate or mononuclear pincer can be stereo-selectively obtained from the same chiral ligand. Their catalytic properties have been demonstrated with the asymmetric FC alkylation reactions.

Graphical abstract: Dinuclear helicate or mononuclear pincer lanthanide complexes from one ligand: stereo-controlled assembly and catalysis
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Sodium cation-templated synthesis of an ion-pair binding heteroditopic [2]catenane

A novel method utilising sodium cation templation between a pyridinium bridged calix[4]diquinone macrocycle and a pyridine-N-oxide functionalised macrocycle precursor motif is used for the construction of a mechanically interlocked ion-pair.

Graphical abstract: Sodium cation-templated synthesis of an ion-pair binding heteroditopic [2]catenane
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Synthetic platform for mono-functionalised tridentate macrocycles as key precursors of mechanically-linked macromolecular systems

Macrocycles bearing a variety of functional groups give access to a wide range of synthetic methods for further derivatisation or preparation of more complex structures such as mechanically interlocked molecules or polymeric materials.

Graphical abstract: Synthetic platform for mono-functionalised tridentate macrocycles as key precursors of mechanically-linked macromolecular systems
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Dynamics of mechanically bonded macrocycles in radial hetero[4]catenane isomers

A pair of radial [4]catenane isomers interlocked with two CB[6]s and one β-CD is reported. Due to the different positions of the tightly bound CB[6]s, shuttling dynamics of the β-CD between the two biphenyl stations are different in the isomers.

Graphical abstract: Dynamics of mechanically bonded macrocycles in radial hetero[4]catenane isomers
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Reversible fluorescence modulation through the photoisomerization of an azobenzene-bridged perylene bisimide cyclophane

An azobenzene-bridged perylene bisimide cyclophane was designed and synthesized, which showed reversible fluorescence intensity switching under light-irradiation due to cooperative adjustments of PBI–PBI and PBI–Azo interactions.

Graphical abstract: Reversible fluorescence modulation through the photoisomerization of an azobenzene-bridged perylene bisimide cyclophane
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Diverse binding of cationic guests by highly substituted [3 + 3] Schiff-base macrocycles

Schiff-base macrocycles interact with ammonium-based guests to form threaded pseudorotaxanes or unthreaded external complexes, and tautomerize in the process.

Graphical abstract: Diverse binding of cationic guests by highly substituted [3 + 3] Schiff-base macrocycles
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Template-driven construction of [8]-imidazolium macrocycles

A controllable and efficient template-driven strategy for the rational construction of polyimidazolium macrocycles has been developed.

Graphical abstract: Template-driven construction of [8]-imidazolium macrocycles
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

A self-assembled tetrathiafulvalene box

A M8L2 metalla-cage constructed through coordination-driven self-assembly from a quinonato bis-ruthenium complex and an electron-rich tetrathiafulvalene (TTF) tetrapyridyl ligand is depicted.

Graphical abstract: A self-assembled tetrathiafulvalene box
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Exploring the tubular self-assembly landscape of dinucleobase amphiphiles in water

The tubular aqueous assembly of dinucleobase amphiphilic monomers endowed with anionic, neutral or cationic groups is investigated under diverse conditions.

Graphical abstract: Exploring the tubular self-assembly landscape of dinucleobase amphiphiles in water
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Orientation of the α-CD component of [2]rotaxanes affects their specific molecular recognition behaviour

An α-CD component enhanced the anion recognition ability of the urea moiety and the deprotonation of the phenol moiety in the axle component in orientationally isomeric [2]rotaxanes with the OH groups on the wide rim of the α-CD, respectively.

Graphical abstract: Orientation of the α-CD component of [2]rotaxanes affects their specific molecular recognition behaviour
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Construction of organometallic trefoil knots and one-dimensional chains featuring half-sandwich Cp*Rh corner units and an abnormal zwitterion ligand

An abnormal flexible O-coordinated zwitterion ligand L shows self-adaptive conformation behaviour in chemical self-assembly. Two trefoil knots were obtained with C-shaped ligand L and two novel 1D chains were obtained with Z-shaped ligand L.

Graphical abstract: Construction of organometallic trefoil knots and one-dimensional chains featuring half-sandwich Cp*Rh corner units and an abnormal zwitterion ligand
From the themed collection: Macrocycle-based Supramolecular Elements
Research Article

Cucurbituril-assisted formation of tunable carbon dots from single organic precursors in water

A facile method by utilizing the host–guest interaction of Q[n]s for the catalytic fabrication of CDs with high emitting qualities and a tunable particle size from a single organic precursor in water with high output has been demonstrated.

Graphical abstract: Cucurbituril-assisted formation of tunable carbon dots from single organic precursors in water
From the themed collection: Macrocycle-based Supramolecular Elements
45 items

About this collection

Welcome to Organic Chemistry Frontiers  themed collection on macrocycle-based supramolecular elements

Supramolecular chemistry evolved from research on macrocycles. Macrocycles are most suitable hosts for guest encapsulation by noncovalent interactions. They also serve as building blocks for constructing high-level molecular and supramolecular architectures and molecular devices, and afford advanced materials.  

Guest edited by Hai-Bo Yang (East China Normal University) and Christoph A. Schalley (Freie Universität Berlin), this themed collection dedicates to the fundamental role of macrocycles as supramolecular elements for the further development of chemistry. 

More articles will be added as soon as they are published. 

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