Binding Ability and Assembly Behavior of <i>β</i>-Cyclodextrin Complexes with 2,2‘-Dipyridine and 4,4‘-Dipyridine

Liu, Yu; Zhao, Yanli; Zhang, Heng Yi; Yang, En Cui; Guan, Xu Dong

doi:10.1021/jo035868x

Cited by 31 publications

(18 citation statements)

References 49 publications

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“…However, the common cone‐shape of TCAS in 3 is disrupted by 4‐DPD, which forms complicated intermolecular hydrogen‐bonding interactions and enforces a novel 1,2‐alternate conformation. In light of the 1,3‐alternate conformer of CAS stabilized by 4,4′‐DPD,29 one may reasonably deduce that the difference of the heteroatom position in DPD plays a critical role in influencing the conformational features and even assembly behavior of the host molecules, which is in agreement with our previous results 30…”

Section: Resultssupporting

confidence: 86%

The Structures and Thermodynamics of Complexes between Water‐Soluble Calix[4]arenes and Dipyridinium Ions

et al. 2004

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Three crystalline complexes were prepared by the inclusion complexation of p‐sulfonatothiacalix[4]arene (TCAS) and p‐sulfonatocalix[4]arene (CAS) with 2,2′‐dipyridinium (2‐DPD; (complexes 1 and 2, respectively), and TCAS with 4,4′‐dipyridinium (4‐DPD; complex 3). The crystal structures show that the calixarenes in 1 and 2 maintain their original cone conformation, with shallow inclusion of 2‐DPD, and assemble themselves into bi‐layer arrangements. However, the cone shape of TCAS in 3 is disrupted by 4‐DPD to assume the so‐called 1,2‐alternate conformation in the solid state, which is similar to the 1,3‐alternate case of CAS stabilized by 4‐DPD (4). The thermodynamics of this inclusion complexation were further investigated by microcalorimetric titration in aqueous solution. The obtained results indicated that the molecular binding ability and selectivity of TCAS/CAS with DPDs is entirely controlled by enthalpy gains accompanied by a smaller negative entropic change; these are discussed from the viewpoint of electrostatic, hydrogen‐bonding, π‐stacking, and van der Waals interactions, size/shape‐fit, and a desolvation effect between host and guest. The molecular selectivity for the inclusion complexation of 2‐DPD with CAS was found to be nine times greater than that of 4‐DPD with CAS. Combining the present crystal structures and thermodynamic parameters revealed that the position of the nitrogen atoms in the DPDs is the crucial factor for controlling the binding modes, molecular selectivity, conformational features, and assembly behavior of the host upon complexation with TCAS/CAS. This will help us to design large molecular assemblies possessing highly supramolecular architectures based on calixarenes by controlling exactly the guest molecules. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Resultssupporting

confidence: 86%

The Structures and Thermodynamics of Complexes between Water‐Soluble Calix[4]arenes and Dipyridinium Ions

et al. 2004

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“…Secondly, the calculated distance between neighbouring CD shields in a tetragonal fashion is ∼0.23 nm ( Supplementary Fig. 19b ), in perfect agreement with the reported distance of hydrogen bond 54 55 , indicating the favourable lateral interaction between the narrow rings of neighbouring CD-shielded cations. Of course, besides the planar square framework, the steric tetrahedron binding style is also possible theoretically.…”

Section: Resultssupporting

confidence: 84%

Flexible single-layer ionic organic–inorganic frameworks towards precise nano-size separation

et al. 2016

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Consecutive two-dimensional frameworks comprised of molecular or cluster building blocks in large area represent ideal candidates for membranes sieving molecules and nano-objects, but challenges still remain in methodology and practical preparation. Here we exploit a new strategy to build soft single-layer ionic organic–inorganic frameworks via electrostatic interaction without preferential binding direction in water. Upon consideration of steric effect and additional interaction, polyanionic clusters as connection nodes and cationic pseudorotaxanes acting as bridging monomers connect with each other to form a single-layer ionic self-assembled framework with 1.4 nm layer thickness. Such soft supramolecular polymer frameworks possess uniform and adjustable ortho-tetragonal nanoporous structure in pore size of 3.4–4.1 nm and exhibit greatly convenient solution processability. The stable membranes maintaining uniform porous structure demonstrate precisely size-selective separation of semiconductor quantum dots within 0.1 nm of accuracy and may hold promise for practical applications in selective transport, molecular separation and dialysis systems.

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“…The binding constant K a [M −1 ] between 2,2′-bipyridyl and βCD was determined to be 1.0 × 10 2 (D 2 O, 298 K) by a 1 H NMR titration experiment (Supplementary Figs 1,2)43, which showed a modest affinity of 2,2′-bipyridyl to the cavity of βCD. The inclusion was also confirmed by using their acrylamide derivatives, βCDAAm and bpyAAm (Supplementary Fig.…”

Section: Resultsmentioning

confidence: 99%

A metal–ion-responsive adhesive material via switching of molecular recognition properties

et al. 2014

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Common adhesives stick to a wide range of materials immediately after they are applied to the surfaces. To prevent indiscriminate sticking, smart adhesive materials that adhere to a specific target surface only under particular conditions are desired. Here we report a polymer hydrogel modified with both β-cyclodextrin (βCD) and 2,2′-bipyridyl (bpy) moieties (βCD–bpy gel) as a functional adhesive material responding to metal ions as chemical stimuli. The adhesive property of βCD–bpy gel based on interfacial molecular recognition is expressed by complexation of metal ions to bpy that controlled dissociation of supramolecular cross-linking of βCD–bpy. Moreover, adhesion of βCD–bpy gel exhibits selectivity on the kinds of metal ions, depending on the efficiency of metal–bpy complexes in cross-linking. Transduction of two independent chemical signals (metal ions and host–guest interactions) is achieved in this adhesion system, which leads to the development of highly orthogonal macroscopic joining of multiple objects.

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Binding Ability and Assembly Behavior of β-Cyclodextrin Complexes with 2,2‘-Dipyridine and 4,4‘-Dipyridine

Cited by 31 publications

References 49 publications

The Structures and Thermodynamics of Complexes between Water‐Soluble Calix[4]arenes and Dipyridinium Ions

The Structures and Thermodynamics of Complexes between Water‐Soluble Calix[4]arenes and Dipyridinium Ions

Flexible single-layer ionic organic–inorganic frameworks towards precise nano-size separation

A metal–ion-responsive adhesive material via switching of molecular recognition properties

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