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Themed collection Supramolecular chemistry in OBC

46 items
Communication

Photodeamination to quinone methides in cucurbit[n]urils: potential application in drug delivery

A prodrug is encapsulated in CB[7] and is photochemically transformed into an active drug inside this supramolecular complex.

Graphical abstract: Photodeamination to quinone methides in cucurbit[n]urils: potential application in drug delivery
From the themed collection: Supramolecular chemistry in OBC
Communication

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.

Graphical abstract: Stereo- and regioselective photocycloaddition of extended alkenes using γ-cyclodextrin
From the themed collection: Supramolecular chemistry in OBC
Communication

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.

Graphical abstract: Tuning the fluorescence of tetraphenylethylene in dilute solutions via modulating multiple-hydrogen-bonding interactions between a Hamilton receptor and cyanuric acid
Communication

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.

Graphical abstract: Intramolecularly enhanced molecular tweezers with unusually strong binding for aromatic guests in unfavorable solvents
From the themed collection: Supramolecular chemistry in OBC
Communication

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.

Graphical abstract: Binding-promoted chemical reaction in the nanospace of a binding site: effects of environmental constriction
From the themed collection: Supramolecular chemistry in OBC
Communication

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.

Graphical abstract: Aromatically functionalized pseudo-crown ethers with unusual solvent response and enhanced binding properties
From the themed collection: Supramolecular chemistry in OBC
Communication

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.

Graphical abstract: Narcissistic chiral self-sorting of molecular face-rotating polyhedra
From the themed collection: Supramolecular chemistry in OBC
Communication

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.

Graphical abstract: Taking advantage of Co(ii) induced enhanced VCD for the fast and sensitive determination of enantiomeric excess
From the themed collection: Supramolecular chemistry in OBC
Paper

Understanding coordination equilibria in solution and gel-phase [2]rotaxanes

An active-metal template approach has been use to synthesise solution and surface bound addressable [2]rotaxanes giving unique insights into thermodynamic equilibria in interlocked structures.

Graphical abstract: Understanding coordination equilibria in solution and gel-phase [2]rotaxanes
From the themed collection: Supramolecular chemistry in OBC
Paper

Cyclic arylopeptoid oligomers: synthesis and conformational propensities of peptide-mimetic aromatic macrocycles

Dynamic macrocyclic peptide-mimetic molecule bearing sequence-controlled side chains.

Graphical abstract: Cyclic arylopeptoid oligomers: synthesis and conformational propensities of peptide-mimetic aromatic macrocycles
From the themed collection: Supramolecular chemistry in OBC
Paper

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.

Graphical abstract: New tetralactam hosts for squaraine dyes
From the themed collection: Supramolecular chemistry in OBC
Paper

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.

Graphical abstract: Synthesis and Suzuki–Miyaura cross coupling reactions for post-synthetic modification of a tetrabromo-anthracenyl porphyrin
From the themed collection: Supramolecular chemistry in OBC
Paper

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.

Graphical abstract: Design of C2-symmetric alkaloidal chiral amphiphiles and configurational effects on self-assembly
From the themed collection: Supramolecular chemistry in OBC
Paper

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.

Graphical abstract: Dynamic Diels–Alder reactions of maleimide–furan amphiphiles and their fluorescence ON/OFF behaviours
From the themed collection: Supramolecular chemistry in OBC
Paper

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.

Graphical abstract: Hydrogen-bonded six-component assembly for capsule formation based on tetra(4-pyridyl)cavitand and isophthalic acid linker and its application to photoresponsive capsule
From the themed collection: Supramolecular chemistry in OBC
Paper

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.

Graphical abstract: Geometric deconstruction of core and electron activation of a π-system in a series of deformed porphyrins: mimics of heme
From the themed collection: Supramolecular chemistry in OBC
Paper

An alternative route for the synthesis of hydroxylated pillar[5]arene-based amphiphiles

Hydroxylated pillar[5]arene-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.

Graphical abstract: An alternative route for the synthesis of hydroxylated pillar[5]arene-based amphiphiles
From the themed collection: Supramolecular chemistry in OBC
Paper

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.

Graphical abstract: Optimized synthesis and indium complex formation with the bifunctional chelator NODIA-Me
From the themed collection: Supramolecular chemistry in OBC
Paper

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 cucurbit[8]uril 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.

Graphical abstract: A supramolecular red to near-infrared fluorescent probe for the detection of drugs in urine
From the themed collection: Supramolecular chemistry in OBC
Paper

Inherently chiral cone-calix[4]arenes 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-calix[4]arenes allows the preparation of inherently chiral derivatives.

Graphical abstract: Inherently chiral cone-calix[4]arenes via a subsequent upper rim ring-closing/opening methodology
From the themed collection: Synthetic methodology in OBC
Paper

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.

Graphical abstract: Biosurfactant-functionalized porphyrin chromophore that forms J-aggregates
From the themed collection: Supramolecular chemistry in OBC
Paper

Light-driven exchange between extended and contracted lasso-like isomers of a bistable [1]rotaxane

A photoactive hydrogen-bonded lasso having an amide-based [1]rotaxane structure has been constructed from acyclic precursors through a self-templating approach. The stability, structural integrity and switching are described.

Graphical abstract: Light-driven exchange between extended and contracted lasso-like isomers of a bistable [1]rotaxane
From the themed collection: Supramolecular chemistry in OBC
Paper

Grafting of porphyrin oligomers on single-walled carbon nanotubes by Hay coupling

Two different Zn-porphyrin oligomers were synthesized on single-walled carbon nanotubes via Hay coupling and the formation of 1,3-butadiyne linkers.

Graphical abstract: Grafting of porphyrin oligomers on single-walled carbon nanotubes by Hay coupling
From the themed collection: Supramolecular chemistry in OBC
Paper

Tuning the biomimetic performances of 4-hydroxyproline-containing cyclic peptoids

Five new cyclic peptoids containing (2S,4R)-4-hydroxyproline (Hyp) residues have been designed and synthesized using a mixed “submonomer/monomer” approach.

Graphical abstract: Tuning the biomimetic performances of 4-hydroxyproline-containing cyclic peptoids
From the themed collection: Supramolecular chemistry in OBC
Paper

A glycoluril dimer–triptycene hybrid receptor: synthesis and molecular recognition properties

We report the preparation of methylene bridged glycoluril dimer 1 bearing two triptycene walls and its function as a host toward hydrophobic cations in water.

Graphical abstract: A glycoluril dimer–triptycene hybrid receptor: synthesis and molecular recognition properties
From the themed collection: Supramolecular chemistry in OBC
Open Access Paper

Campestarenes: new building blocks with 5-fold symmetry

New campestarene derivatives bear functional groups designed to facilitate the formation of supramolecular assemblies of these 5-fold symmetric building blocks.

Graphical abstract: Campestarenes: new building blocks with 5-fold symmetry
From the themed collection: Supramolecular chemistry in OBC
Open Access Paper

Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties

The different host–guest behaviour of non-interconvertible bis-porphyrin tweezer isomers was examined, contributing to ongoing discussions regarding rigidity/flexibility and preorganisation in synthetic receptors.

Graphical abstract: Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties
From the themed collection: Supramolecular chemistry in OBC
Paper

“Choose-a-size” control in the synthesis of sucrose based urea and thiourea macrocycles

High yield synthesis of either monomeric or dimeric sucrose-based macrocycles is just a matter of choice – flow or batch synthesis.

Graphical abstract: “Choose-a-size” control in the synthesis of sucrose based urea and thiourea macrocycles
From the themed collection: Supramolecular chemistry in OBC
Paper

Chemoenzymatic macrocycle synthesis using resorcylic acid lactone thioesterase domains

Resorcylate acid lactone thioesterases can synthesize a variety of macrolactone and macrolactams, as well as a cyclicdepsipeptide.

Graphical abstract: Chemoenzymatic macrocycle synthesis using resorcylic acid lactone thioesterase domains
From the themed collection: Synthetic methodology in OBC
Paper

An electron-transfer induced conformational transformation: from non-cofacial “sofa” to cofacial “boat” in cyclotetraveratrylene (CTTV) and formation of charge transfer complexes

Cyclotetraveratrylene (CTTV) undergoes oxidation-induced folding, consistent with interconversion from a non-cofacial “sofa” conformation to a cofacial “boat” conformer.

Graphical abstract: An electron-transfer induced conformational transformation: from non-cofacial “sofa” to cofacial “boat” in cyclotetraveratrylene (CTTV) and formation of charge transfer complexes
From the themed collection: Supramolecular chemistry in OBC
Paper

Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry

The first series of discrete multichromophore DBTAA arrays have been synthesized from the parent macrocycle and its asymmetrical relatives in 40–46% isolated yields.

Graphical abstract: Multichromophore arrays of dibenzotetraaza[14]annulene: a promising platform for bioorganic chemistry
From the themed collection: Supramolecular chemistry in OBC
Paper

Inhibition of the prototropic tautomerism in chrysazine by p-sulfonatocalixarene hosts

This study reveals the unusual inhibition of excited-state prototropic tautomerism of Chrysazine by p-sulfonatocalix[4,6]arene hosts.

Graphical abstract: Inhibition of the prototropic tautomerism in chrysazine by p-sulfonatocalixarene hosts
From the themed collection: Supramolecular chemistry in OBC
Open Access Paper

Backbone conformation affects duplex initiation and duplex propagation in hybridisation of synthetic H-bonding oligomers

Forming the first intramolecular H-bond is straightforward, but forming subsequent intramolecular interactions is difficult, because the backbone imposes more severe constraints.

Graphical abstract: Backbone conformation affects duplex initiation and duplex propagation in hybridisation of synthetic H-bonding oligomers
From the themed collection: Supramolecular chemistry in OBC
Paper

Effects of cucurbit[n]uril (n = 7, 8, 10) hosts on the formation and stabilization of a naphthalenediimide (NDI) radical anion

The binding interactions of a NDI diammonium dichloride salt with cucurbit[n]uril (CB[n], n = 7,8, 10) and the formation process of a NDI radical anion upon photoexcitation of the NDI derivative in the presence of a CB[n] host have been investigated.

Graphical abstract: Effects of cucurbit[n]uril (n = 7, 8, 10) hosts on the formation and stabilization of a naphthalenediimide (NDI) radical anion
From the themed collection: Supramolecular chemistry in OBC
Paper

Push–pull quinoidal porphyrins

Quinoidal porphyrins with electron-donating 1,3-dithiolane and electron-withdrawing dicyanomethylene groups form tightly π-stacked layer structures, despite their curved geometries and bulky aryl substituents. The crystal structures of these quinoidal porphyrins indicate that there is no significant contribution from singlet biradical or zwitterionic resonance forms.

Graphical abstract: Push–pull quinoidal porphyrins
From the themed collection: Supramolecular chemistry in OBC
Paper

Readily functionalized AAA–DDD triply hydrogen-bonded motifs

Herein we present a new, readily functionalized AAA–DDD hydrogen bond array.

Graphical abstract: Readily functionalized AAA–DDD triply hydrogen-bonded motifs
From the themed collection: Supramolecular chemistry in OBC
Paper

An aryl-fused redox-active tetrathiafulvalene with enhanced mixed-valence and radical-cation dimer stabilities

Enhanced mixed-valence and radical-cation dimer stabilities were found for an extended tetrathiafulvalene.

Graphical abstract: An aryl-fused redox-active tetrathiafulvalene with enhanced mixed-valence and radical-cation dimer stabilities
From the themed collection: Supramolecular chemistry in OBC
Paper

Disulphide bond exchange inhibited by air – kinetic and thermodynamic products in a library of macrocyclic cysteine derivatives

Oxidation of dithiols provides strained monomeric macrocycles which transform upon disulphide bond exchange into stable dimers.

Graphical abstract: Disulphide bond exchange inhibited by air – kinetic and thermodynamic products in a library of macrocyclic cysteine derivatives
From the themed collection: Supramolecular chemistry in OBC
Paper

Understanding the conformational analysis of gababutin based hybrid peptides

A new class of gababutin-based tetrapeptide shows a C12/C10 hydrogen-bonded hybrid turn.

Graphical abstract: Understanding the conformational analysis of gababutin based hybrid peptides
From the themed collection: Supramolecular chemistry in OBC
Paper

Supramolecular chiroptical switching of helical-sense preferences through the two-way intramolecular transmission of a single chiral source

Complexation-induced reversal of helical-sense preferences is demonstrated with a simple molecule with a pair of exciton-coupled chromophores.

Graphical abstract: Supramolecular chiroptical switching of helical-sense preferences through the two-way intramolecular transmission of a single chiral source
Paper

Neutral glycoconjugated amide-based calix[4]arenes: complexation of alkali metal cations in water

Novel water-soluble calix[4]arene glycoconjugates with efficient cation-binding sites were synthesized and their complexation reactions in methanol and aqueous solutions were studied.

Graphical abstract: Neutral glycoconjugated amide-based calix[4]arenes: complexation of alkali metal cations in water
From the themed collection: Supramolecular chemistry in OBC
Paper

Unexpected cleavage of upper rim-bridged calix[4]arenes leading to linear oligophenolic derivatives

Upper rim-bridged calix[4]arenes possess an unprecedented reactivity as a consequence of their high internal strain imposed by the single bond bridge.

Graphical abstract: Unexpected cleavage of upper rim-bridged calix[4]arenes leading to linear oligophenolic derivatives
From the themed collection: Supramolecular chemistry in OBC
Paper

Complete tetraglycosylation of a calix[4]arene by a chemo-enzymatic approach

It was demonstrated that a calixarene can be a substrate for glycosyltransferases and thanks to an exhaustive glycosylation a multivalent tetralactosaminyl calix[4]arene was obtained.

Graphical abstract: Complete tetraglycosylation of a calix[4]arene by a chemo-enzymatic approach
From the themed collection: Supramolecular chemistry in OBC
Paper

A modular approach towards functionalized highly stable self-complementary quadruple hydrogen bonded systems

This article reports a new class of highly reactive dithiane-tethered self-complementary quadruple hydrogen-bonded systems without having prototropy-related issues. These systems further reacted with different amines to form highly stable molecular duplexes.

Graphical abstract: A modular approach towards functionalized highly stable self-complementary quadruple hydrogen bonded systems
From the themed collection: Supramolecular chemistry in OBC
Paper

Conformational isomerism in cyclic peptoids and its specification

Conformational chirality is an emerging and neglected property of rigid cyclic peptoids determining structural, catalytic, and biological properties. The present contribution analyzes its impact and sets the configurational rules to define it.

Graphical abstract: Conformational isomerism in cyclic peptoids and its specification
From the themed collection: Supramolecular chemistry in OBC
Paper

Improved synthesis of symmetrically & asymmetrically N-substituted pyridinophane derivatives

Reported herein is an optimized, larger-scale synthesis of symmetric and asymmetric pyridinophane tetraazamacrocycles, which are versatile ligands in coordination chemistry.

Graphical abstract: Improved synthesis of symmetrically & asymmetrically N-substituted pyridinophane derivatives
From the themed collection: Supramolecular chemistry in OBC
46 items

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The latest articles published in Organic and Biomolecular Chemistry related to supramolecular chemistry research.

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