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.
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.
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.
A styryl based fluorogenic probe with high affinity for a cyclodextrin derivative
A styryl-based fluorogenic near-IR probe registers a very high association constant with sulfobutylether substituted β-cyclodextrin host, having prospects as biological marker and improved pH and temperature sensor.
Preparation of a large-sized highly flexible carbon nanohoop
A highly flexible carbon nanohoop composed of HBC panels was prepared by connection together with biphenylene spacers.
Symmetrically backfolded molecules emulating the self-similar features of a Sierpinski triangle
A Sierpinski molecule with symmetrically backfolded branches has been synthesized to present a complex, self-similar system of conjugated aromatic backbones featuring three distinct levels on the structural hierarchy.
A dimethoxypillararene/azastilbene host–guest recognition motif and its applications in the fabrication of polypseudorotaxanes
A host–guest recognition motif based on 1,4-dimethoxylpillararene (DMP5) and guest trans-4,4′-vinylenedipyridine (trans-G1) was fabricated and applied to construct metallosupramolecular polypseudorotaxanes.
A click mediated route to a novel fluorescent pyridino-extended calixpyrrole sensor: synthesis and binding studies
This new calipyrrole entity displays molecular fluorescence recognition capabilities towards iron and mercury which are major environmental contaminants.
Triaminopyrimidine derivatives as transmembrane HCl transporters
A series of triaminopyrimidine-based anion transporters has been described, capable of diminishing proton gradients across lipid bilayers at physiologically relevant pH.
Triazole functionalized acyclic cucurbit[n]uril-type receptors: host·guest recognition properties
The synthesis, characterization, and molecular recognition properties of 2–4 toward organic ammonium ions in water is reported.
Carboxylated pillar[n]arene (n = 5–7) host molecules: high affinity and selective binding in water
A systematic study of host–guest chemistry for water-soluble pillar[n]arenes in water.
Synthesis, structure, and anion binding of functional oxacalixarenes
Oxacalixarenes obtained from the highly efficient, one-pot SNAr reaction were post-macrocyclization functionalized through the reduction of nitro groups and hydrolysis of the ester groups to obtain several derivatives of desired solubility and anion binding property.
A phototunable anion receptor for C–H⋯X interactions with benzoate anions
A phototunable receptor binds to anions in one of its photoisomeric forms via CH⋯X interaction.
Covalently linked meso-tetraaryl triphyrin(2.1.1)-ferrocene(s) conjugates: synthesis and properties
Functionalized meso-tetraaryl triphyrins(2.1.1) containing two meso-iodophenyl groups or a bromo group at the β-pyrrole carbon were synthesized over a sequence of steps.
Substituent-controlled racemization of dissymmetric coordination capsules
We report the effect of substituents (methyl, isopropyl, methoxy, and methoxyphenyl) at the 6′-position of the 2,2′-bipyridyl arms on the racemization of dissymmetric coordination capsules 1a–d.
Functional self-assembled nanovesicles based on β-cyclodextrin, liposomes and adamantyl guanidines as potential nonviral gene delivery vectors
Multicomponent supramolecular nanovesicles functionalized with adamantyl guanidines were prepared.
Systematic rim cyano-functionalization of pillararene and corresponding host–guest property varieties
Synthetic investigation of the systematic replacement of alkoxy groups in pillararene by cyano ones was carried out. Host–guest property studies of nCN-pillararenes and 1,4-dicyanobutane showed the functionization number related host–guest interaction varieties.
Transmembrane H+/Cl− cotransport activity of bis(amido)imidazole receptors
Bis(amide) appended imidazole having a sickle-shaped trivalent hydrogen-bonding structure reported as a transmembrane H+/Cl− symporter.
Synthesis and characterization of propeller-shaped mono- to hexacationic quinolinium-substituted benzenes
In propeller-shaped molecules a central benzene core is substituted by up to six N-methylquinolinium rings.
Control of conformation in α-helix mimicking aromatic oligoamide foldamers through interactions between adjacent side-chains
Hydrogen-bonding interactions are used to bias the conformation of an aromatic oligoamide foldamer in favour of an α-helix mimicking syn conformer.
Doxorubicin-reinforced supramolecular hydrogels of RGD-derived peptide conjugates for pH-responsive drug delivery
Doxorubicin reinforced the self-assembly of RGD-derived peptide conjugates responsive to mild acidity.
Aggregation-induced emission and polymorphism/shape/size-dependent emission behaviours of fenamates for potential drug evaluation
Aggregation-induced emission and polymorphism/shape/size-dependent emission behaviors were found coexisting in fenamates, which provides a novel approach toward future drug evaluation.
Rapid one-pot synthesis of pyrrole-appended isocorroles
Free-base meso-triarylcorroles and pyrrole undergo oxidative coupling in dichloromethane in the presence of DDQ affording 35–60% yields of 5/10-pyrrole-appended isocorroles in a matter of seconds.
High photodynamic activities of water-soluble inclusion complexes of 5,15-diazaporphyrins in cyclodextrin
Inclusion complexes of 5,15-diazaporphyrin derivatives in trimethyl-β-cyclodextrin exhibited high photodynamic activity under visible-light irradiation at wavelengths greater than 620 nm.
Dicyclohexylurea derivatives of amino acids as dye absorbent organogels and anion sensors
Dicyclohexyl urea (DCU) derivatives of amino acids Fmoc-Phe-DCU (M1), Fmoc-Phg-DCU (M2) and Fmoc-Gaba-DCU (M3) have been shown to form phase selective, thermoreversible and mechanically robust gels in a large range of organic solvents. Organogels act as dye adsorbants and M1–M3 act as selective anion sensors for F−, OH− and OAc−.
Playing supramolecular dominoes with light: building and breaking a photoreversible G-quadruplex made from guanosine, boric acid and an azobenzene
Addition of an azo dye triggers a cascade of photoreversible intermolecular recognition processes in a mixture of simple guanosine derivatives.
Promotion of the collagen triple helix in a hydrophobic environment
The collagen triple helix is better suited for octanol than for water.
Self-templated synthesis of amide catenanes and formation of a catenane coordination polymer
A metal-free synthesis of catenanes is exploited to prepare an interlocked ligand that self-assembles with Ag(I) to form one-dimensional metallo-polycatenanes.
Salts accelerate the switching kinetics of a cyclobis(paraquat-p-phenylene) rotaxane
The switching speed of a bistable rotaxane upon oxidation is found to be increased in the presence of added salts.
FRET-based nanosensors for monitoring and quantification of alcohols in living cells
Upon binding of alcohols, ObpIIa undergoes conformational changes resulting in transfer of energy in the form of FRET from donor to the acceptor fluorophore.
Quadruply N-methylated octaphyrin: a helical macrocycle exhibiting chiroptical properties and dynamic conformation changes correlated with helical and inner N-methyl orientations
Octaphyrin(220.127.116.11.18.104.22.168) bearing four methyl moieties at the inner nitrogen sites has been synthesized and exhibited chiroptical properties and dynamic conversions.
Kinetic and spectroscopic studies on the chiral self-aggregation of amphiphilic zinc and copper (L)-prolinate-tetraarylporphyrin derivatives in different aqueous media
The chiral self-aggregation of (L)-proline porphyrin derivatives depends on both the nature of the media and the coordinated metal ion.
Supramolecular self-assembly of fluorescent peptide amphiphiles for accurate and reversible pH measurement
We report the synthesis and self-assembly of fluorescent peptide amphiphiles (NBD-PA) composed of a fluorescent NBD probe and a peptide derivative VVAADD with a C12-alkyl-chain as the linker (NBD-C12-VVAADD).
Design of C2-symmetric alkaloidal chiral amphiphiles and configurational effects on self-assembly
Alkaloidal chiral amphiphiles composed of C2-symmetric bispyrrolidinoindoline scaffold were developed, where the configurational differences significantly influenced the chiroptical, dynamic and supramolecular properties.
New tetralactam hosts for squaraine dyes
Tetralactam macrocycles with similar substituents (methyl, methoxy, methylenedioxy) on the macrocycle aromatic sidewalls have very different squaraine recognition properties.
Understanding coordination equilibria in solution and gel-phase rotaxanes
An active-metal template approach has been use to synthesise solution and surface bound addressable rotaxanes giving unique insights into thermodynamic equilibria in interlocked structures.
Cyclic arylopeptoid oligomers: synthesis and conformational propensities of peptide-mimetic aromatic macrocycles
Dynamic macrocyclic peptide-mimetic molecule bearing sequence-controlled side chains.
Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin
A tetra-bromoanthracenylporphyrin was synthesised and its reactivity was tested by post-synthetic modification using the Suzuki–Miyaura cross coupling reaction.
Dynamic Diels–Alder reactions of maleimide–furan amphiphiles and their fluorescence ON/OFF behaviours
Dynamic Diels–Alder additions of maleimide–furan amphiphiles lead to reversible fluorescence ON/OFF behaviours and exchange of furan moieties.
Hydrogen-bonded six-component assembly for capsule formation based on tetra(4-pyridyl)cavitand and isophthalic acid linker and its application to photoresponsive capsule
Two molecules of tetra(4-pyridyl)cavitand 1 and four molecules of isophthalic acid derivatives 2 self-assemble into a hydrogen-bonded six-component capsule 12·24.
Geometric deconstruction of core and electron activation of a π-system in a series of deformed porphyrins: mimics of heme
The predominant distortion of heme is responsible for its electronic activity, catalytic ability and spectral properties.
An alternative route for the synthesis of hydroxylated pillararene-based amphiphiles
Hydroxylated pillararene-based amphiphiles were synthesized by a co-cyclization strategy followed by catalytic hydrogenation. This approach unlocks the synthesis and the design of a wide range of structural manipulations to these amphiphilic pillararenes.
Optimized synthesis and indium complex formation with the bifunctional chelator NODIA-Me
Multi-step synthetic route provides the ligand NODIA-Me in high yield. Radiolabeling with [111In]InCl3 yields stable complexes in high radiochemical purity and yield.
A supramolecular red to near-infrared fluorescent probe for the detection of drugs in urine
A host–guest complex based on a newly designed and synthesized cationic perylene dye and cucurbituril exhibits red-NIR emission, high affinity and stability, and large Stokes shift. It can serve as a red-NIR fluorescent displacement probe for the detection of drugs in urine.
Inherently chiral cone-calixarenes via a subsequent upper rim ring-closing/opening methodology
The introduction of a lactone moiety spanning the distal positions in the upper rim of cone-calixarenes allows the preparation of inherently chiral derivatives.
Biosurfactant-functionalized porphyrin chromophore that forms J-aggregates
Synthesis of sophorolipid-porphyrin conjugates with built-in variations in non-covalent interactions, H–bonding, π–π stacking, and hydrophobic interactions for supramolecular self-assembly.
Light-driven exchange between extended and contracted lasso-like isomers of a bistable rotaxane
A photoactive hydrogen-bonded lasso having an amide-based rotaxane structure has been constructed from acyclic precursors through a self-templating approach. The stability, structural integrity and switching are described.
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The latest articles published in Organic and Biomolecular Chemistry related to supramolecular chemistry research.