Molecular tweezers and clips as synthetic receptors. Molecular recognition and dynamics in receptor-substrate complexes.

  title={Molecular tweezers and clips as synthetic receptors. Molecular recognition and dynamics in receptor-substrate complexes.},
  author={F G Kl{\"a}rner and Bj{\"o}rn Kahlert},
  journal={Accounts of chemical research},
  volume={36 12},
The molecular tweezers (1, 2) and clips (3-7) containing naphthalene and benzene spacer units can be synthesized via repetitive Diels-Alder reactions by the use of a molecular "Lego" set consisting of bisdienophiles (8, 9, 14) and dienes (10, 13). The new receptors selectively bind electron-deficient neutral and cationic substrates in solution. Only the benzene-spaced tweezers form complexes with aliphatic substrates, whereas the other receptors bind aromatic substrates preferentially. HPLC… 
Towards the design of neutral molecular tweezers for anion recognition.
The stabilization trend reflected by the energetic results when fluorine substituents were added to benzene rings confirms the hypothesis about the possibility of obtaining neutral tweezers composed of aromatic rings that can bind anions.
Dynamics in host-guest complexes of molecular tweezers and clips.
A detailed analysis of the kinetic and thermodynamic data suggests that in the transition state of dissociation the guest molecule is still clipped between the aromatic tips of the host molecule.
Effect of molecular clips and tweezers on enzymatic reactions by binding coenzymes and basic amino acids
The tetramethylene-bridged molecular tweezers bearing lithium methanephosphonate or dilithium phosphate substituents in the central benzene or naphthalene spacer-unit and the dimethylene-bridged
Dynamic molecular tweezers composed of dibenzocyclooctatetraene units: synthesis, properties, and thermochromism in host-guest complexes.
5 b, which has CH(2)OMe groups on the COT rings and longer ethoxy groups onThe terminal benzene rings, showed the highest electron density of the cavity and hence the highest binding ability with the electron-deficient guest molecules.
Synthesis and Guest Recognition of Switchable Pt-Salphen Based Molecular Tweezers
In this present study, the synthesis of switchable molecular tweezers composed of a central terpyridine unit substituted in 4,4″ positions by two Pt(II)-salphen complexes is reported, enabling a reverse control of the mechanical motion compared to the previously reported 6,6″ substituted terp Pyridine-based tweezer.
Molecular tweezers: concepts and applications.
  • J. Leblond, A. Petitjean
  • Chemistry, Biology
    Chemphyschem : a European journal of chemical physics and physical chemistry
  • 2011
At the crossroad between flexible and rigid spacers, stimulus-responsive molecular tweezers controlled by ionic, redox or light triggers belong to the realm of molecular machines, and, applied to molecular tweezing, open doors to the selective binding, transport and release of their cargo.
Glycoluril-Derived Molecular Clips are Potent and Selective Receptors for Cationic Dyes in Water.
The cavity of 1 is shaped by aromatic surfaces of negative electrostatic potential and therefore displays high affinity and selectivity for planar and cationic aromatic guests that distinguishes it from CB[n] receptors that prefer aliphatic over aromatic guests.
Aromatic interactions by molecular tweezers and clips in chemical and biological systems.
The ability of molecular tweezers to cap critical lysine residues can be used to interfere with the pathology of protein misfolding diseases such as Alzheimer's disease, because many of them involve noncovalent interactions with these critical residues during their early stages.


Molecular Tweezers as Synthetic Receptors: Molecular Recognition of Electron‐Deficient Aromatic Substrates by Chemically Bonded Stationary Phases
The synthesis and chromatographic properties of novel chemically-bonded stationary phases CBSP-1 and CBSP-2, containing substituted molecular tweezers with benzene and naphthalene spacer-units, are
Synthesis and supramolecular properties of trimethylene-bridged clips.
The novel trimethylene-bridged clips 3 and 4 have been synthesized by using repetitive stereoselective Diels-Alder reactions of the benzo- and naphthobismethylenenorbornenes as dienes and norbornadiene 9 as bisdienophile to serve as receptors for a variety of electron-deficient neutral and cationic aromatic substrates, comparable to the molecular tweezers 1 and 2.
Modeling of Supramolecular Properties of Molecular Tweezers, Clips, and Bowls
Abstract The electrostatic potential surface (EPS) is calculated for molecular tweezers, clips, and bowls at different levels of theory (semiempirical AM1, ab initio HF/6-31G*, and density functional
Molecular recognition in aqueous media. New binding studies provide further insights into the cation-π interaction and related phenomena
A large number of binding studies in aqueous media designed to provide new insights into noncovalent binding interactions, especially the cation-π interaction are described, finding that, in addition to the alkyliminium and tetraalkylammonium guests, sulfonium and guanidinium guests also show substantial cations-π effects.
Molecular tweezers as synthetic receptors: molecular recognition of electron-deficient aromatic and aliphatic substrates.
The molecular tweezers 1 and 2 are selective receptors for electron-deficient aromatic and aliphatic substrates forming, for example, complexes with onium salts such as N-methylpyrazinium iodide,
A study of a moleculartweezer host-guest system by a combination of quantum-chemical calculations and solid-state NMR experiments.
A study of a host-guest system consisting of a naphthalene-spaced tweezer with a 1,4 dicyanobenzene guest molecule is presented and the convergence with respect to the size of the solid-state fragment is investigated.
Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry.
This Account is a compilation of recent literature covering the syntheses of the homologues and derivatives, and their supramolecular chemistry of cucurbituril, a synthetic receptor.
Aromatic-aromatic interaction: a mechanism of protein structure stabilization.
Analysis of neighboring aromatic groups in four biphenyl peptides or peptide analogs and 34 proteins reveals a specific aromatic-aromatic interaction that helps stabilize tertiary structure, and 20 percent stabilize quaternary structure.