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.
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.
Targeted synthesis of meso-aryl substituted aromatic trans-doubly N-confused dithia/diselena  porphyrins (18.104.22.168) 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.
Multi-stimuli controlled release of transmembrane chloride ion carrier from sulfonium-linked procarrier
Guest-induced supramolecular chirality transfer in pseudorotaxanes: experimental and computational study
We constructed several pseudorotaxanes via chiral binaphthalene crown ethers and achiral ammonium salts, and found that the binaphthalene groups can induce new CD signals only in the pseudorotaxane between the hosts and the guest with anthryl.
Synthesis of 2-bromo- and 2-phenyl-neo-confused porphyrins
New examples of neo-confused porphyrins are reported. These retain global diatropic characteristics but are relatively unstable in solution.
Synthesis of N-acetylglucosamine and N-acetylallosamine resorcinarene-based multivalent β-thio-glycoclusters: unexpected affinity of N-acetylallosamine ligands towards Wheat Germ Agglutinin
Resorcinarene-based glycoclusters bearing β-S-GlcNAc and β-S-AllNAc residues were synthesized and ITC and molecular docking calculations provided evidence of their strong affinity towards WGA.
Improved water solubility and photodynamic activity of hydroxy-modified porphyrins by complexation with cyclodextrin
TMe-β-CDx-complexed porphyrins with hydroxyphenyl moieties in the meso-position showed higher photodynamic activities than TMe-β-CDx-complexed porphyrins with dihydroxyphenyl moieties and porphyrins injected in a dimethyl sulfoxide solution.
Absolute handedness control of oligoamide double helices by chiral oxazolylaniline induction
Aromatic oligoamide double helices bearing a chiral oxazolylaniline moiety were synthesized and their helix handedness was completely controlled (de > 99%).
An amide hydrogen bond templated rotaxane displaying a peptide motif – demonstrating an expedient route to synthetic mimics of lasso peptides
The rapid synthesis and characterization of an amide hydrogen bond templated rotaxane – demonstrating a potential pathway to synthetic analogues of lasso peptides.
Influence of cyclic and acyclic cucurbiturils on the degradation pathways of the chemical warfare agent VX
Cucurbituril and an acyclic cucurbituril cause the chemical warfare agent VX to preferentially decompose in basic aqueous solution under C–S bond cleavage rather than by the normally preferred hydrolysis of the P–O and P–S bonds.
An electrochemically controlled supramolecular zip tie based on host–guest chemistry of CB
A stimuli-responsive supramolecular assembly based on a bipyridinium thread and CB behaves like a zip tie relaxing the chain as a consequence of the insertion of both radical cation moieties within the CB macrocycle.
Selective functionalization of 6-amino-6-methyl-1,4-perhydrodiazepine for the synthesis of a library of polydentate chelators
AMPED-based [un]symmetrical ligands having different numbers and types of donor atoms to bind metal ions were synthesized for diagnostic applications.
Synthesis and stereoisomerism of [n]cyclo-2,9-phenanthrenylene congeners possessing alternating E/Z- and R/S-biaryl linkages
A novel series of cycloarylenes with blended E/Z and R/S linkages were synthesized, and their cyclostereoisomerism was investigated.
Enhanced ion binding by the benzocrown receptor and a carbonyl of the aminonaphthalimide fluorophore in water-soluble logic gates
Fluorescent logic gates with benzocrown ethers attached at the imide naphthalimide exhibit synergistic binding of Na+ and K+ in aqueous methanol and water.
One-pot synthesis of porphyrin-based rotaxanes
Rotaxanes prepared in a one-pot reaction via simultaneous threading-followed-by-stoppering and condensation can be used to generate different co-conformational states making these systems potential multi-state switches.
Towards new nanoporous biomaterials: self-assembly of sulfopillararenes with vitamin D3 into supramolecular polymers
The ability of novel sulfopillararenes to form UV stable inclusion complex with cholecalciferol (vitamin D3) was shown.
Controlling the liberation rate of the in situ release of a chemical fuel for the operationally autonomous motions of molecular machines
Aminolysis of the anhydride of 2-cyano-2-phenylpropanoic acid can be employed to conveniently regulate the liberation rate of the related acid which, in turn, can be used as a fuel for acid–base operated molecular machines.
Selective fluorescence sensing of H2PO4− by the anion induced formation of self-assembled supramolecular polymers
H2PO4− anions induced the formation of a fluorescent supramolecular polymer by halogen bonding interactions in a bromoimidazolium based tripodal receptor.
Preparation of cage-shaped hexakis(spiroborate)s
Direct construction of anionic hexakis(spiroborate) prismatic cages was realized by the reaction of hexahydroxytriphenylene, bis(dihydroxynaphthalene)s, and boric acid.
Construction of pH sensitive smart glutathione peroxidase (GPx) mimics based on pH responsive pseudorotaxanes
Two pH-sensitive smart glutathione peroxidase (GPx) mimics were developed by using pH-responsive pseudorotaxanes based on cucurbituril and organoselenium compounds.
I2-Catalyzed transformation of o-aminobenzamide to o-ureidobenzonitrile using isothiocyanates
The present work describes an unexpected and unique protocol for the iodine catalysed synthesis of o-ureidobenzonitriles using o-aminobenzamides and isothiocyanates via intramolecular rearrangement.
Host–guest interaction of nitroxide radicals with water-soluble pillararenes
The host–guest interaction of nitroxide radicals with water-soluble pillararenes has been for the first time verified in this study.
Encapsulation of ionic liquids inside cucurbiturils
Stable host–guest inclusion complexes are formed between cucurbiturils and ionic liquids in water.
Mono-functionalized derivatives and revised configurational assignment of amide naphthotubes
A pair of mono-functionalized amide naphthotubes with one alkyne and three carboxylate groups has been synthesized, and they show different binding behavior from its parent naphthotubes, presumably due to the self-inclusion of the alkyne group.
Quantification of cooperativity in the self-assembly of H-bonded rosettes
The effective molarity associated with the macrocyclisation step in the self-assembly of triaminopyrimidines with barbiturates and with cyanates was measured as 2 M.
Cucurbituril as a catalytic nanoreactor for one-pot synthesis of isoxazolidines in water
The main objective of supramolecular chemistry is to mimic the macrosystems present in nature, a goal that fits perfectly with the green chemistry guidelines.
Self-assembly of amphiphilic aryl-squaramides in water driven by dipolar π–π interactions
Amphiphilic aryl-squaramides self-assemble via unprecedented dipolar π–π interactions forming well-defined supramolecular aggregates and self-consistent hydrogels in water
Complexation of 5-aminovaleric acid zwitterions in aqueous/methanol solution by heterotopic tri-cationic receptors
Heterotopic tri-cationic receptor based on 4,10,16-triaza-18-crown-6 is capable of efficient and selective binding of the zwitterionic form of 5-aminovaleric acid (5-AVA) in aqueous/methanol solution.
Cucurbituril-driven modulation of ligand–DNA interactions by ternary assembly
Cucurbituril induces a change in the ligand–DNA binding mode and destroys dye aggregates templated by DNA through the formation of a ternary complex.
Synthesis and chiroptical properties of cylindrical macrocycles comprising two calixaramide moieties
Novel chiral macrocyclic aromatic amides of medium molecular weight were synthesized by the one-step amide coupling of a bis(alkylamino)terphenyl diacid as monomer.
Molecular replication using covalent base-pairs with traceless linkers
Covalent template-directed synthesis was carried out using an oligomeric template to produce identical copy strands in iterative rounds of replication.
Effects of nano-confinement and conformational mobility on molecular imprinting of cross-linked micelles
Confining molecular imprinting in the nanospace of a micelle yielded highly selective protein-mimicking nanoparticle receptors to distinguish closely related water-soluble guests.
Optically active Ag(I): o-OPE helicates using a single homochiral sulfoxide as chiral inducer
Preferred-handed helical folding of OPEs achieved by just one chiral motif: changes in CD spectra after Ag(I) complexation.
Three-state switching in a double-pole change-over nanoswitch controlled by redox-dependent self-sorting
Entangled toggling leads to a rare case of a double-pole change-over switching. Since two connections are cleaved in a correlated manner, it represents an intriguing modus operandi of molecular nanoswitching.
Dynamic optical activity induction in the N-alkyl-N′-trityl ureas and thioureas
Stereodynamic trityl group, utilized as a reporter of chirality, hampers hydrogen bonding network in optically active urea and thiourea derivatives.
A calixarene with acylguanidine units as an efficient catalyst for phosphodiester bond cleavage in RNA and DNA model compounds
Conjugated carbonyl units in a calixarene scaffold provide the right amount of flexibility for catalysis with a minimum entropic cost.
Solid–liquid extraction of iodide and bromide from aqueous media by a new water-insoluble phenoxycalixpyrrole-epichlorohydrin polymer
A phenoxycalixpyrrole-epichlorohydrin based extractant was easily synthesized for the first time and used for iodide and bromide extraction from aqueous media.
Stereoselective deconjugation of macrocyclic α,β-unsaturated esters by sequential amidation and olefin transposition: application to enantioselective phase-transfer catalysis
The stereoselective synthesis of chiral macrocycles bearing two aliphatic amide functional groups is reported.
About this collection
The latest articles published in Organic and Biomolecular Chemistry related to supramolecular chemistry research.