Pseudorotaxane

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Feihe Huang - One of the best experts on this subject based on the ideXlab platform.

Haibo Yang - One of the best experts on this subject based on the ideXlab platform.

  • supramolecular polymer cross linked by discrete tris 2 Pseudorotaxane metallacycles and its redox responsive behavior
    Inorganic Chemistry, 2018
    Co-Authors: Xuqing Wang, Lijun Chen, Guangqiang Yin, Bo Jiang, Haibo Yang
    Abstract:

    A new discrete hexagonal metallacycle M containing tris-[2]Pseudorotaxane moiety has been successfully designed and synthesized via coordination-driven self-assembly. The newly designed tris-[2]Pseudorotaxane metallacycle was well characterized with nuclear magnetic resonance and mass spectra analysis. Such tris-[2]Pseudorotaxane metallacycle M and pillar[5]arene dimer (PD) could further form a new family of cross-linked redox-responsive supramolecular polymer M⊃(PD)3 through a host–guest interaction. Interestingly, the polymer M⊃(PD)3 displayed redox-responsive behavior and showed tuned weight-average diffusion coefficients D upon redox stimuli, which is attributed to the changed coordination geometries of [Cu(phen)2]+ and [Cu(phen)2]2+ in such system.

  • Supramolecular Polymer Cross-Linked by Discrete Tris-[2]Pseudorotaxane Metallacycles and Its Redox-Responsive Behavior
    2018
    Co-Authors: Xuqing Wang, Lijun Chen, Guangqiang Yin, Bo Jiang, Haibo Yang
    Abstract:

    A new discrete hexagonal metallacycle M containing tris-[2]­Pseudorotaxane moiety has been successfully designed and synthesized via coordination-driven self-assembly. The newly designed tris-[2]­Pseudorotaxane metallacycle was well characterized with nuclear magnetic resonance and mass spectra analysis. Such tris-[2]­Pseudorotaxane metallacycle M and pillar[5]­arene dimer (PD) could further form a new family of cross-linked redox-responsive supramolecular polymer M⊃(PD)3 through a host–guest interaction. Interestingly, the polymer M⊃(PD)3 displayed redox-responsive behavior and showed tuned weight-average diffusion coefficients D upon redox stimuli, which is attributed to the changed coordination geometries of [Cu­(phen)2]+ and [Cu­(phen)2]2+ in such system

Xuqing Wang - One of the best experts on this subject based on the ideXlab platform.

  • supramolecular polymer cross linked by discrete tris 2 Pseudorotaxane metallacycles and its redox responsive behavior
    Inorganic Chemistry, 2018
    Co-Authors: Xuqing Wang, Lijun Chen, Guangqiang Yin, Bo Jiang, Haibo Yang
    Abstract:

    A new discrete hexagonal metallacycle M containing tris-[2]Pseudorotaxane moiety has been successfully designed and synthesized via coordination-driven self-assembly. The newly designed tris-[2]Pseudorotaxane metallacycle was well characterized with nuclear magnetic resonance and mass spectra analysis. Such tris-[2]Pseudorotaxane metallacycle M and pillar[5]arene dimer (PD) could further form a new family of cross-linked redox-responsive supramolecular polymer M⊃(PD)3 through a host–guest interaction. Interestingly, the polymer M⊃(PD)3 displayed redox-responsive behavior and showed tuned weight-average diffusion coefficients D upon redox stimuli, which is attributed to the changed coordination geometries of [Cu(phen)2]+ and [Cu(phen)2]2+ in such system.

  • Supramolecular Polymer Cross-Linked by Discrete Tris-[2]Pseudorotaxane Metallacycles and Its Redox-Responsive Behavior
    2018
    Co-Authors: Xuqing Wang, Lijun Chen, Guangqiang Yin, Bo Jiang, Haibo Yang
    Abstract:

    A new discrete hexagonal metallacycle M containing tris-[2]­Pseudorotaxane moiety has been successfully designed and synthesized via coordination-driven self-assembly. The newly designed tris-[2]­Pseudorotaxane metallacycle was well characterized with nuclear magnetic resonance and mass spectra analysis. Such tris-[2]­Pseudorotaxane metallacycle M and pillar[5]­arene dimer (PD) could further form a new family of cross-linked redox-responsive supramolecular polymer M⊃(PD)3 through a host–guest interaction. Interestingly, the polymer M⊃(PD)3 displayed redox-responsive behavior and showed tuned weight-average diffusion coefficients D upon redox stimuli, which is attributed to the changed coordination geometries of [Cu­(phen)2]+ and [Cu­(phen)2]2+ in such system

Xuzhou Yan - One of the best experts on this subject based on the ideXlab platform.

  • n Pseudorotaxanes n 2 3 from self assembly of two cryptands and a 1 2 bis 4 pyridinium ethane derivative
    European Journal of Organic Chemistry, 2012
    Co-Authors: Xuzhou Yan, Peifa Wei, Mingming Zhang, Xiaodong Chi, Feihe Huang
    Abstract:

    Efficient host–guest complexation and interesting self-assembled structures formed between two crown ether-based cryptands and a 1,2-bis(4-pyridinium)ethane derivative 3 are reported. By self-assembly of cis-dibenzo-24-crown-8-based cryptand 1 and guest 3, a [3]Pseudorotaxane was formed in solution, which further formed a supramolecular poly[3]Pseudorotaxane structure in the solid state driven by π-π stacking interactions. Meanwhile, a [2]Pseudorotaxane, obtained from self-assembly of a bis(m-phenylene)-32-crown-10-based cryptand 2 and guest 3, can form a supramolecular poly[2]Pseudorotaxane structure in the solid state. This difference in the binding model reflects the diversity of host–guest chemistry of crown ether-based cryptands. Furthermore, these host–guest recognition processes and self-assembled structures were fully characterized by 1H NMR, UV/Vis spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray analysis. Interestingly, formation of the [3]Pseudorotaxane between cryptand 1 and guest 3 can be reversibly controlled by adding and removing potassium cations in acetone. This reversible complexation process provides a simple on/off mechanism that can be used in the construction of controllable molecular switches.

  • a chemical responsive bis m phenylene 32 crown 10 2 7 diazapyrenium salt 2 Pseudorotaxane
    Chemical Communications, 2012
    Co-Authors: Xuzhou Yan, Peifa Wei, Mingming Zhang, Feihe Huang
    Abstract:

    A chemical-responsive bis(m-phenylene)-32-crown-10/2,7-diazapyrenium salt [2]Pseudorotaxane was prepared. It was found to form a supramolecular poly[2]Pseudorotaxane in the solid state driven by π–π stacking interactions.

  • A chemical-responsive bis(m-phenylene)-32-crown-10/2,7-diazapyrenium salt [2]Pseudorotaxane
    Chemical communications (Cambridge England), 2012
    Co-Authors: Xuzhou Yan, Peifa Wei, Mingming Zhang, Feihe Huang
    Abstract:

    A chemical-responsive bis(m-phenylene)-32-crown-10/2,7-diazapyrenium salt [2]Pseudorotaxane was prepared. It was found to form a supramolecular poly[2]Pseudorotaxane in the solid state driven by π–π stacking interactions.

  • [2]Pseudorotaxanes based on the recognition of cryptands to vinylogous viologens.
    Organic letters, 2011
    Co-Authors: Xuzhou Yan, Peifa Wei, Mingming Zhang, Xiaodong Chi, Jiyong Liu, Feihe Huang
    Abstract:

    Host–guest complexation between two crown ether-based cryptands and two vinylogous viologens has been studied. Formation of [2]Pseudorotaxanes from a dibenzo-24-crown-8-based cryptand and these vinylogous viologens can be reversibly controlled by adding and removing potassium cation in acetone. Furthermore, the complexation between a bis(m-phenylene)-32-crown-10-based cryptand and a vinylogous viologen exhibits a high association constant, 1.18 × 106 M–1 in acetone, and leads to the formation of a supramolecular poly[2]Pseudorotaxane in the solid state.

J. Fraser Stoddart - One of the best experts on this subject based on the ideXlab platform.

  • Kinetically controlled self-assembly of Pseudorotaxanes on crystallization.
    Organic letters, 2006
    Co-Authors: Brian H. Northrop, Saeed J. Khan, J. Fraser Stoddart
    Abstract:

    Mixing of equimolar amounts of cyclobis(paraquat-p-phenylene) (CBPQT4+) with a bis-4-methylphenyl ether (MPE twice) of a 1,5-dioxynaphthalene (DNP) derivative in MeCN/CH2Cl2 (3:1) results in the formation of a [2]Pseudorotaxane which, on crystallization, yields a [4]Pseudorotaxane in the solid state that is stabilized by multiple [C−H···F] interactions:  a mixture of the same components in a 1:3 ratio affords a crystalline [2]Pseudorotaxane after vapor diffusion of methyl-tert-butyl ether into a solution of these components in MeCN/CH2Cl2 (3:1).

  • In the twilight zone between [2]Pseudorotaxanes and [2]rotaxanes.
    Chemistry (Weinheim an der Bergstrasse Germany), 2003
    Co-Authors: Jan O. Jeppesen, Scott A. Vignon, J. Fraser Stoddart
    Abstract:

    A [2]Pseudorotaxane, based on a semi-dumbbell-shaped component containing asymmetrically substituted monopyrrolotetrathiafulvalene and 1,5-dioxynaphthalene recognition sites for encirclement by cyclobis(paraquat-p-phenylene) and with a "speed bump" in the form of a thiomethyl group situated between the two recognition sites, has been self-assembled. This supramolecular entity is a mixture in solution of two slowly interconverting [2]Pseudorotaxanes, one of which is on the verge of being a [2]rotaxane at room temperature, allowing it to be isolated by employing flash column chromatography. These two [2]Pseudorotaxanes were both characterized in solution by UV/Vis and 1 H NMR spectroscopies (1D and 2D) and also by differential pulse voltammetry. The spectroscopic and electrochemical data reveal that one of the complexes behaves wholly as a [2]Pseudorotaxane, while the other has some [2]rotaxane character to it. The kinetics of the shuttling of cyclobis(paraquat-p-phenylene) between the monopyrrolotetrathiafulvalene and the 1,5-dioxynaphthalene recognition sites have been investigated at different temperatures. The shuttling processes, which are accompanied by detectable color changes, can be monitored using UV/Vis and 1 H NMR spectroscopies; the spectroscopic data have been employed in the determination of the rate constants, free energies of activation, enthalpies of activation, and the entropies of activation for the translation of cyclobis(paraquat-p-phenylene) between the two recognition sites.

  • X-ray Crystallographic Studies on the Noncovalent Syntheses of Supermolecules
    Structural Chemistry, 1999
    Co-Authors: Matthew C. T. Fyfe, J. Fraser Stoddart, David J. Williams
    Abstract:

    An approach to the supramolecular syntheses of discrete multicomponent aggregates of noncovalently bound molecules, i.e., supermolecules, is described. This approach involved the careful analysis of X-ray crystal structures so as to permit a gradual increase in superstructural complexity. Many elaborate supermolecules were synthesized noncovalently from dialkylammonium-containing cations and crown ethers, following the initial observation that the dibenzylammonium ion threads through dibenzo[24]crown-8 to generate a singly stranded, singly encircled [2]Pseudorotaxane, principally as a result of $$[{\text{N}}^{\text{ + }} - {\text{H}} \cdot \cdot \cdot {\text{O}}]$$ and $$[{\text{C}} - {\text{H}} \cdot \cdot \cdot {\text{O}}]$$ hydrogen bond formation. The scope of the fundamental recognition motif obtained from this initial observation was then broadened, through the use of thread-like ions with multiple dialkylammonium centers and/or larger crown ethers, so that multiply stranded and/or multiply encircled Pseudorotaxanes could be prepared. Cations bearing both dialkylammonium and crown ether recognition sites were also used for the nocovalent synthesis of a discrete daisy chain supermacrocycle and the basic recognition motif was combined with other motifs for the production of a wide range of novel superarchitectures. As a greater understanding of the noncovalent interactions governing the self-assembly of the complex superarchitectures was acquired, new protocols for the noncovalent syntheses of doubly docked Pseudorotaxanes and interwoven supramolecular bundles, including a supramolecular analogue of the photosynthetic special pair, were developed. The discovery that anions can play a prominent role in the solid-state self-assembly of some of the supermolecules was a valuable spinoff of the research.

  • Interwoven supramolecular arrays via the noncovalent polymerization of Pseudorotaxanes
    Coordination Chemistry Reviews, 1999
    Co-Authors: Matthew C. T. Fyfe, J. Fraser Stoddart
    Abstract:

    Abstract This review describes how the noncovalent polymerization of Pseudorotaxanes—inclusion complexes in which thread-like molecules or ions interpenetrate macrorings’ central cavities without the formation of a mechanical bond—leads to the production of interwoven supramolecular arrays in the solid state. The noncovalent synthesis of these polymeric supramolecular architectures requires the independent and simultaneous operation of at least two different orthogonal recognition algorithms, viz. a threading algorithm, for the formation of the Pseudorotaxane, and a noncovalent polymerization algorithm, that permits interPseudorotaxane association in the crystal. The information required for the operation of these orthogonal recognition algorithms is preprogrammed into the covalent frameworks of the interwoven supramolecular arrays’ precursors. Several different types of intermolecular interactions have been employed by crystal engineers for the noncovalent synthesis of interwoven supramolecular arrays in the solid state, in particular, metal–ligand, π – π stacking and hydrogen bonding interactions.

  • Doubly Docked Pseudorotaxanes
    Chemistry - A European Journal, 1998
    Co-Authors: Peter R. Ashton, J. Fraser Stoddart, Matthew C. T. Fyfe, M.‐victoria Martínez‐díaz, Stephan Menzer, Cesare Schiavo, Andrew J. P. White, David J. Williams
    Abstract:

    The snug fit of two suitably spaced dialkylammonium centers within the cavity of the macrocyclic polyether bis-p-phenylene[34]crown-10 (BPP34C10) generates [2]Pseudorotaxanes in which each cationic ammonium center “docks” with one of the macrocycle's two polyether loops (right), for the most part by means of hydrogen bonds. One such doubly docked [2]Pseudorotaxane forms the basis of a prototypical chromophoric supramolecular switch triggered by alterations to the surrounding pH.