Themed collection Supramolecular chemistry in OBC
Recent advances on triptycene derivatives in supramolecular and materials chemistry
Molecular cages for biological applications
This review compiles selected relevant examples of synthetic receptors defining a closed three-dimensional cavity (cages) with applications in chemical biology and biomedicine.
Indicator displacement assays: from concept to recent developments
This review lays emphasis on background concept and summarizes the recent developments of various competitive IDAs. Moreover, current challenges relating to the development of new IDAs and potential future perspectives revealing the fate of IDAs have also been given.
Phosphorus containing porous organic polymers: synthetic techniques and applications in organic synthesis and catalysis
This review features the recent advancement made in phosphorus-containing POPs, highlighting different synthetic techniques for their preparation and application in organic synthesis.
Crown ether–pillararene hybrid macrocyclic systems
In this review, we will fully discuss the synthesis/preparation and applications of crown ether–pillararene hybrid macrocyclic systems/compounds.
Molecular recognition and sensing of dicarboxylates and dicarboxylic acids
This review outlines challenges faced in recognition and detection of dicarboxylic acids and dicarboxylates and strategies used to obtain effective and observable interactions in the period from 2014 to 2020.
Synthetic strategies towards mechanically interlocked oligomers and polymers
Synthetic methodologies towards the preparation of oligomeric and polymeric mechanically interlocked molecules are described, including both covalent strategies and self-assembly approaches.
The synthesis and applications of porphyrin-containing pillararenes
Recent progress regarding the combination of porphyrins and pillararenes into hybrid compounds and supramolecular systems is summarized in this review.
Enantioselective synthesis enabled by visible light photocatalysis
This review summarizes recent developments in visible-light enantioselective photocatalysis reactions, which provide convenient and effective tools for asymmetric synthesis.
Macrocyclization via C–H functionalization: a new paradigm in macrocycle synthesis
The emergence and applications of the C–H activation logic as a new paradigm in macrocyclization reactions are captured in this review.
Supramolecular assembly of functional peptide–polymer conjugates
The following review gives an overview about synthetic peptide–polymer conjugates as macromolecular building blocks and their self-assembly into a variety of supramolecular architectures, from supramolecular polymer chains, to anisotropic 1D arrays, 2D layers, and more complex 3D networks.
Tetrathiafulvalene-calixpyrrole: a versatile synthetic receptor for electron-deficient planar and spherical guests
The chemistry of tetrathiafulvalene-calixpyrrole is reviewed with focus on conformational behavior, receptor properties and ionically controlled electron transfer processes.
Supramolecular vesicles based on pillar[n]arenes: design, construction, and applications
Recent progress in supramolecular vesicles based on pillar[n]arenes is reviewed.
Glutamate carboxypeptidase II as a model system for designing host–guest units: a theoretical approach
Through a combined crystallographic and computational analysis, we designed and investigated two novel host units for the recognition of neutral and charged guests inspired by a glutamate carboxypeptidase II system and its inhibitors.
Halogen bonding effect on electrochemical anion oxidation in ionic liquids
The properties of three imidazolium based ionic liquids have been compared and used as solvents for the electrochemical oxidation of various anions.
New antimicrobial self-assembling short lipopeptides
Short lipopeptides, that self-assemble into supramolecular structures, show antimicrobial activity.
Calixarene-decorated liposomes for intracellular cargo delivery
Liposomes equipped at the outer membrane with positively charged calixarenes show improved efficiency in cargo delivery. This is facilitated by the interaction between the macrocycle units and heparan sulfate proteoglycans surrounding the cell.
Comparison of [Pd2L4][BF4]4 cages for binding of n-octyl glycosides and nitrate (L = isophthalamide or dipicolinamide linked dipyridyl ligand)
Isophthalamide (X = CH) and a dipicolinamide (X = N) derived dipyridyl ligands both form a [Pd2L4][BF4]4 cage in solution, but only the isophthalamide derived cage easily binds to glycosides and nitrate.
Chalcogen bonding mediates the formation of supramolecular helices of azapeptides in crystals
Supramolecular M- and P-helices are formed via intermolecular S⋯S and S⋯O chalcogen bonding of alanine-based azapeptides containing a β-turn structure and equipped with a thiophene group at the N- or C-terminus, respectively.
Water binding stabilizes stacked conformations of ferrocene containing sheet-like aromatic oligoamides
The encapsulation of discrete water molecules in flexible sheet-like aromatic oligoamide foldamers, as evidenced by structural and spectroscopic studies, stabilizes their structure.
An easily accessible, lower rim substituted calixarene selectively binds N,N-dimethyllysine
A single substitution on p-sulfonatocalixarene, away from its binding face, modifies its selectivity towards a smaller and less hydrophobic guest (dimethyllysine) without making direct contact with the guest.
Facile access to foldable redox-active flavin-peptide conjugates
A convenient approach for the synthesis of foldable redox-active flavin peptide conjugates was established.
Supramolecular brush polymers prepared from 1,3,4-oxadiazole and cyanobutoxy functionalised pillararene for detecting Cu2+
The self-assembly of an A1/A2 disubstituted pillararene was used to construct a supramolecular brush polymer.
Mukaiyama aldol reaction catalyzed by (benz)imidazolium-based halogen bond donors
A Mukaiyama aldol reaction can be catalyzed by bidentate halogen bond donors with very high efficiency. The halogenated catalysts were stable over multiple consecutive runs, which supports the halogen-bond-based mode of catalysis.
A medium-firm drug-candidate library of cryptand-like structures on T7 phage: design and selection of a strong binder for Hsp90
We designed and synthesized a library of cryptand-like structures on the T7 phage; a strong binder for a cancer-related protein was selected from the library.
Aptamer protective groups tolerate different reagents and reactions for regioselective modification of neomycin B
The aptameric protective group strategy is compatible with diverse reagents and reaction conditions for the synthesis of new neomycin B derivatives.
Targeted synthesis of meso-aryl substituted aromatic trans-doubly N-confused dithia/diselena  porphyrins (22.214.171.124) with NIR absorption: spectroscopic and theoretical characterization
N-TIPS pyrrole and thiophene/selenophene dicarbinol: the two most promising and significant building blocks made for each other for constructing highly aromatic and NIR absorptive trans-doubly N-confused porphyrins.
A fully synthetic 6-aza-artemisinin bearing an amphiphilic chain generates aggregates and exhibits anti-cancer activities
Appendage of an amphiphilic chain by exploiting the nitrogen installed on the 6-aza-artemisinin imparted self-assembling properties. The fully synthetic 6-aza-artemisinin formed aggregates and exhibited increased in vitro anti-cancer activities.
Deprotection of a benzyl unit induces a 22π aromatic macrocycle of 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption
We report a deprotection-induced aromaticity switching from nonaromatic to a 22π aromatic macrocycle of 3-oxypyripentaphyrin(0.1.1.1.0) with strong NIR absorption.
Characterization in aqueous medium of an FMN semiquinone radical stabilized by the enzyme-like microenvironment of a modified polyethyleneimine
The elusive flavin semiquinone intermediate found in flavoproteins such as cryptochromes has been obtained in aqueous solution by single electron reduction of the natural FMN cofactor using sodium ascorbate.
Hierarchical self-assembly of an azobenzene dyad with inverted amide connection into toroidal and tubular nanostructures
Inversion of the amide connectivity of an azobenzene dyad, which self-assembles into chiral toroids and nanotubes, improves the thermal stability of the assemblies, however it negatively affects supramolecular chirality.
Fluorescent supramolecular hierarchical self-assemblies from glycosylated 4-amino- and 4-bromo-1,8-naphthalimides
The investigation into the self-assembly formation of the glycan based 4-amino- and 4-bromo-1,8-naphthalimide (Nap) structures 1–3 is presented.
Self-assembling purine and pteridine quartets: how do π-conjugation patterns affect resonance-assisted hydrogen bonding?
π-Conjugation patterns determine the association strengths of purine and pteridine quartets.
Probing the determinants of porosity in protein frameworks: co-crystals of cytochrome c and an octa-anionic calixarene
In contrast to sulfonato-calixarene (sclx4), which mediates close-packed assemblies, the higher charge carboxylate-containing sclx4mc induced a crystalline framework of cytochrome c.
Chiral bisphosphine ligands based on quinoline oligoamide foldamers: application in asymmetric hydrogenation
Single-handed quinoline oligoamide foldamer-based bisphosphine ligands that can coordinate with Rh(cod)2BF4 were used as a platform in asymmetric hydrogenation.
Synthesis of helical π-conjugated polymers bearing pyridine N-oxide pendants and asymmetric allylation of aldehydes in the helical cavity
Asymmetric allylation of aldehydes was conducted inside the helical cavity of a helically folded π-conjugated polymer bearing pyridine N-oxide pendants.
Thermodynamically driven self-assembly of pyridinearene to hexameric capsules
For the first time the formation of hexameric pyridinearene capsule has been observed in gas phase, in solution and in solid state. A thermodynamic balance between capsule formation was observed, showing favour to hexamer.
A convenient one-pot nanosynthesis of a C(sp2)–C(sp3)-linked 3D grid via an ‘A2 + B3’ approach
The synthesis of fluorene-based 3D-grid-FTPA, which shows excellent chemical, thermal, and photo-stabilities, has been developed using a one-pot Friedel–Crafts reaction.
meso-Aryl substituted stable unorthodox 5,10-porphodimethenes with α,β and β,β-N-methyl pyrrole connectivities: synthesis and spectroscopic, solid state and theoretical characterization
meso-Aryl substituted highly stable single conformers of doubly mutant porphodimethenes.
Unidirectional complexation of pillararenebenzoquinoneoxime with alkyl alcohols
Unidirectional binding between a pillararenebenzoquinoneoxime host and n-alkyl alcoholic guests was realized with the hydroxy heads of the guests in direct contact with the oxime group of the macrocyclic host.
Acid/base- and base/acid-switchable complexation between anionic-/cationic-pillararenes and a viologen ditosylate salt
Acid/base and base/acid-controllable molecular switches were constructed based on water-soluble anionic pillararene or cationic pillararene and a viologen ditosylate salt.
Acid–base controlled multiple conformation and aromaticity switches in tren-capped hexaphyrins
Upon protonation, a tren-capped hexaphyrin undergoes simple conformational exchanges between rectangular, Möbius and triangular shapes affording different aromaticities and cage environments, and ultimately leading to a host–guest complex.
Using reversible non-covalent and covalent bonds to create assemblies and equilibrating molecular networks that survive 5 molar urea
Molecules that assemble through reversible covalent and noncovalent interactions achieve self-assembly at extreme levels of urea and NaCl.
Photodeamination to quinone methides in cucurbit[n]urils: potential application in drug delivery
A prodrug is encapsulated in CB and is photochemically transformed into an active drug inside this supramolecular complex.
Stereo- and regioselective photocycloaddition of extended alkenes using γ-cyclodextrin
Photoexcitation of dibenzalacetones in homogeneous media and solid state yields a mixture of products with poor conversions. Reactivity of the substrate encapsulated within γ-cyclodextrin results in efficient 2 + 2 photocycloaddition between two reactants on both alkenes groups, yielding a single product with remarkable regio- and stereoselectivity at high conversions.
Tuning the fluorescence of tetraphenylethylene in dilute solutions via modulating multiple-hydrogen-bonding interactions between a Hamilton receptor and cyanuric acid
A hydrogen bonded luminescent supramolecular network from HTPE and CTPE can be further tuned.
Intramolecularly enhanced molecular tweezers with unusually strong binding for aromatic guests in unfavorable solvents
Molecular tweezers using aromatic interactions for binding normally work best in polar instead of nonpolar solvents due to the strong solvophobic effect in the binding.
Binding-promoted chemical reaction in the nanospace of a binding site: effects of environmental constriction
Chemical reactions in a confined nanospace can be very different from those in solution.
Aromatically functionalized pseudo-crown ethers with unusual solvent response and enhanced binding properties
Intramolecularly enhanced flexible receptors outperformed traditional rigid receptors when the direct binding force was weakened by solvent competition.
Narcissistic chiral self-sorting of molecular face-rotating polyhedra
Narcissistic chiral self-sorting prevailed in the assembly of molecular face-rotating polyhedra from a C3h building block 5,5,10,10,15,15-hexabutyl-truxene-2,7,12-tricarbaldehyde and racemic mixtures of 1,2-diamines.
Taking advantage of Co(II) induced enhanced VCD for the fast and sensitive determination of enantiomeric excess
Large Co(II)-induced VCD signals provide a method for determining the enantiomeric excess of α-amino acids. This strategy can be followed for building new VCD protocols.
Gold-Catalyzed Amide-Alkynes Oxidation/Carbene/Alkyne Metathesis: Access to Functionalized γ-Lactams
A reference scale of cucurbituril binding affinities
The binding of the macrocyclic host cucurbituril with selected guest molecules has been re-investigated to cover a large range in affinities (millimolar to femtomolar) and to set up a reference scale for future binding constant determinations.
Duplex vs. folding: tuning the self-assembly of synthetic recognition-encoded aniline oligomers
We present a strategy for characterising and preventing the undesired folding between adjacent units in duplex-forming synthetic hetero-oligomers.
Red-shifted tetra-ortho-halo-azobenzenes for photo-regulated transmembrane anion transport
Squaramide functionalised red-shifted azobenzenes for cooperative anion binding and enhanced photo-regulated transmembrane transport are reported.
Facilitating functionalization of benzene-1,3,5-tricarboxamides by switching amide connectivity
Selective functionalization of C3-symmetrical supramolecular motifs was achieved by switching the amide connectivity of one side chain, yielding supramolecular polymers with a tunable number of functional groups.
Nucleophile-induced transformation of phenoxathiin-based thiacalixarenes
The phenoxathiin-based thiacalixarenes react with NaSH to yield unexpected linear oligomers through a unique cascade of three consequent SNAr reactions triggered by the initial nucleophilic attack of an SH− anion.
Acridinone-based anion transporters
The acridinone 1,9-bis(thio)urea scaffold was repurposed for application in anion transport by appending a variety of electron-withdrawing groups to the peripheral phenyl moieties. High levels of activity were achieved which facilitated strictly electroneutral transport.
Stimuli-responsive transmembrane anion transport by AIE-active fluorescent probes
Anticancer drug resistance implicates multifunctional mechanisms, and hypoxia is one of the key factors in therapeutic resistance. Herein, we report the development of AIE-active Cl− ion transporter which get activated under hypoxic environment.
Structural dynamism of chiral sodium peraza-macrocycle complexes derived from cyclic peptoids
Peraza-macrocycles are the most studied chelating agents. An efficient approach toward chiral cyclen and hexacyclen ligands, starting from cyclic peptoids, is described.
Solvent-directed formation of helically twisted stacking constructs via self-assembly of tris(phenylisoxazolyl)benzene dimers
Ureido-pyrimidinone (UPy)-appended tris(phenylisoxazolyl)benzene dimers were synthesized. The dimers were self-assembled to form helically twisted stacking constructs only in a 40% (v/v) CHCl3/methylcyclohexane mixture.
Fluorescent 4-amino-1,8-naphthalimide Tröger's bases (TBNaps) possessing (orthogonal) ‘α-amino acids’, esters and di-peptides and their solvent dependent photophysical properties
The synthesis of fifteen bis-naphthalimide based Tröger's bases (TBNaps) possessing α-amino acids, esters or dipeptides, from 4-amino-1,8-naphthalimide is described.
Intermolecular binding preferences of haloethynyl halogen-bond donors as a function of molecular electrostatic potentials in a family of N-(pyridin-2-yl)amides
The roles played by halogen bonds and hydrogen bonds in the crystal structures of N-(pyridin-2-yl)amides were evaluated and rationalised in the context of calculated molecular electrostatic potentials.
Steric effects on the intramolecular charge transfer fluorescence of benzo[b]thiophene-1,1-dioxide bridged macrocages
Steric effects on ICT fluorescence were investigated. The Onsager radii for these BTO2s were increased in the following order: TMSBTO2, non-cage isomers, and caged BTO2s.
Assembly and optical properties of 1D helical bundles induced by triphenylamine, side chains and solvents in crystals
Helical foldamers can achieve one-dimensional extended helical assembly by the synergistic action of isobutoxy side chains, triphenylamine and methanol solvent in crystals.
Self-assembly of neutral platinum complexes possessing chiral hydrophilic TEG chains
Neutral platinum complexes that possess chiral triethylene glycol (TEG) moieties were synthesized. The complexes formed chiral micellar aggregates in THF/water mixture.
An unnatural tripeptide structure containing intramolecular double H-bonds mimics a turn hairpin conformation
A series of unnatural tripeptides, each consisting of two aromatic γ-amino acid residues and an ϖ-amino acid residue, are designed to probe their folding into hairpin conformations.
Understanding the binding properties of phosphorylated glycoluril-derived molecular tweezers and selective nanomolar binding of natural polyamines in aqueous solution
Selective nanomolar binding of biological polyamines to a novel glycoluril-derived molecular tweezer is reported. The high selectivity over their biosynthetic precursor may be of interest, as elevated polyamine levels are linked to several diseases.
Chiral figure-eight molecular scaffold for fluorescent probe development
Cell microscopy screening of enantiomeric fluorescent squaraine figure-eight probes reveals a large difference in mitochondrial targeting.
Metal-templated synthesis of rigid and conformationally restricted cyclic bisporphyrins: specific retention times on a cyanopropyl-modified silica gel column
Both the distance and rigidity are important for strong retentions on a cyanopropyl-modified silica gel column.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to supramolecular chemistry research.