29 Works

High Fidelity Kinetic Self-Sorting in Multi-Component Systems Based on Guests with Multiple Binding Epitopes

Lyle Isaacs, Peter Y. Zavalij & Pritam Mukhopadhyay
The molecular recognition platforms of natural systems often possess multiple binding epitopes, each of which has programmed functional consequences. We report the dynamic behavior of a system comprising CB[6], CB[7], and guests cyclohexanediammonium (1) and adamantanealkylammonium (2) that we refer to as a two-faced guest because it contains two distinct binding epitopes. We find that the presence of the two-faced guestjust as is observed for protein targeting in vivodictates the kinetic pathway that the system...

Anion-Free Bambus[6]uril and Its Supramolecular Properties

Jan Svec, Michal Dusek, Karla Fejfarova, Peter Stacko, Petr Klán, Angel E. Kaifer, Wei Li, Edita Hudeckova & Vladimir Sindelar
Abstract Methods for the preparation of anion-free bambus[6]uril (BU6) are presented. They are based on the oxidation of iodide anion, which is bound inside the macrocycle, utilizing dark oxidation...

Water-mediated inclusion of benzoates and tosylates inside the bambusuril macrocycle

Angel E. Kaifer, Vaclav Havel, Vladimir Sindelar & Marek Necas
A supramolecular complex between benzoates and a bambusuril crystallizes out immediately after mixing in chloroform but only in the presence of residual water molecules. In this complex each of the two portals of the macrocycle is occupied by one benzoate. Carboxylate groups are connected through hydrogen bo

Guest Binding Dynamics with Cucurbit[7]uril in the Presence of Cations

Hao Tang, Denis Fuentealba, Young Ho Ko, Narayanan Selvapalam, Kimoon Kim & Cornelia Bohne
The binding dynamics of R-(+)-2-naphthyl-1-ethylammonium cation (NpH+) with cucurbit[7]uril (CB[7]) was investigated. Competitive binding with Na+ or H3O+ cations enabled the reaction to be slowed down sufficiently for the kinetics to be studied by fluorescence stopped-flow experiments. The binding of two Na+ cations to CB[7], i.e., CB[7]·Na+ (K01 = 130 ± 10 M–1) and Na+·CB[7]·Na+ (K02 = 21 ± 2 M–1), was derived from the analysis of binding isotherms and the kinetic studies. NpH+ binds...

Distinct photophysical behaviour and transport of cell-impermeable [Ru(bpy)2dppz]2+ in live cells using cucurbit[7]uril as a delivery system

Meenakshi Shinde, Soniya Rao, Shridhar Gejji & Anupa Kumbhar
We have successfully demonstrated the delivery of a cell-impermeable [Ru(bpy)2dppz]2+ complex across the cell membrane in live cells using a cucurbit[7]uril molecular container.

A Bambusuril Macrocycle that Binds Anions in Water with High Affinity and Selectivity

Vaclav Havel, Vladimir Sindelar & Mirza Arfan Yawer
One ring binds them all: A bambusuril macrocycle is able to selectively capture a large number of different inorganic anions in water. The high stability of the resulting inclusion complexes is due t...

endo-Functionalized molecular tubes: selective encapsulation of neutral molecules in non-polar media

Guobao Huang, Arto Valkonen, Kari Rissanen & Wei Jiang
Four endo-functionalized molecular tubes show high binding affinity and selectivity to neutral molecules.

Real-time analysis of multiple anion mixtures in aqueous media using a single receptor

Vaclav Havel, Vladimir Sindelar & Mirza Arfan Yawer
Bambusuril macrocycles allow qualitative and quantitative sensing of anion mixtures in water using 1H NMR spectroscopy.

Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents

Laura Gilberg, Ben Zhang, Peter Y. Zavalij, Vladimir Sindelar & Lyle Isaacs
A series of glycoluril molecular clips and acyclic CB[n]-type receptors are tested as solubilizing agents for insoluble drugs.

Supramolecular binding and release of sulfide and hydrosulfide anions in water

Julián Vázquez Gonzálvez & Vladimir Sindelar
Bambusuril macrocycles bind and release sulfide and hydrosulfide anions in water.

Supramolecular Storage and Controlled Photorelease of an Oxidizing Agent using a Bambusuril Macrocycle

Vladimir Sindelar, Edoardo Torti, Václav Havel, Mirza A. Yawer, Lucie Ludvíková, Michal Babiak & Petr Klán
Abstract The oxidizing ability of peroxodisulfate upon complexation inside the Bambusuril macrocycle cavity is inhibited. This dianionic agent can be released on demand from its stable 1:1 complex ...

Cucurbit[7]uril⋅Guest Pair with an Attomolar Dissociation Constant

Lyle Isaacs, Peter Y. Zavalij, Liping Cao, Marina Šekutor, Kata Mlinarić-Majerski & Robert Glaser
A perfect pair: The complex between cucurbit[7]uril (CB[7]) and diamantane-4,9-bis(NMe3) (6) has a dissociation constant of 1.4Ã10â18âM in aqueous solution. Competition experiments show that CB[7]â6 ...

Noninnocent Role of Na+ Ions in the Binding of the N-Phenyl-2-naphthylammonium Cation as a Ditopic Guest with Cucurbit[7]uril

Hao Tang, Suma S Thomas & Cornelia Bohne
Na+ ions influence the mechanism for the binding of the ditopic guest N-phenyl-2-naphthylammonium cation (Ph-AH+-Np) to cucurbit[7]uril (CB[7]) by facilitating, at increased Na+ concentrations, the formation of a higher-order complex. Binding of the larger naphthyl moiety of Ph-AH+-Np forms the Ph-AH+-Np@CB[7] 1:1 complex (where “@” represents an inclusion complex) at low Na+ ion concentrations (≤5 mM), whereas the inclusion of the smaller phenyl moiety in CB[7] (CB[7]@Ph-AH+-Np) is transient. Ph-AH+-Np@CB[7] is formed by reactions with...

Anion Binding Inside a Bambus[6]uril Macrocycle in Chloroform

Vaclav Havel & Vladimir Sindelar
Abstract Bambus[6]urils are a class of neutral anion receptors with outstanding binding properties in various solvents. The host–guest associations of bambusurils in aqueous environments have been ...

Determination of the kinetics underlying the pKa shift for the 2-aminoanthracenium cation binding with cucurbit[7]uril

Suma S. Thomas & Cornelia Bohne
The binding dynamics of the 2-aminoanthracenium cation (AH+) and 2-aminoanthracene (A) with cucurbit[7]uril (CB[7]) was studied using stopped-flow experiments. The kinetics was followed by measuring the fluorescence changes over time for AH+ and A, which emit at different wavelengths. The studies at various pH values showed different mechanisms for the formation of the AH+@CB[7] complex, with this complex formed either by the binding of AH+ or by the initial binding of A followed by protonation....

Supramolecular control of phthalocyanine dye aggregation

Vânia F. Pais, Eliana F.A. Carvalho, João P.C. Tomé & Uwe Pischel
(2014). Supramolecular control of phthalocyanine dye aggregation. Supramolecular Chemistry: Vol. 26, Cucurbit[n]uril: Molecular Barrels of Opportunity (ICCB 2013), pp. 642-647.

The Cucurbit[n]uril Family:  Prime Components for Self-Sorting Systems

Simin Liu, Christian Ruspic, Pritam Mukhopadhyay, Sriparna Chakrabarti, Peter Y. Zavalij & Lyle Isaacs
We determined the values of Ka for a wide range of host−guest complexes of cucurbit[n]uril (CB[n]), where n = 6−8, using 1H NMR competition experiments referenced to absolute binding constants measured by UV/vis titration. We find that the larger homologuesCB[7] and CB[8]individually maintain the size, shape, and functional group selectivity that typifies the recognition behavior of CB[6]. The cavity of CB[7] is found to effectively host trimethylsilyl groups. Remarkably, the values of Ka for the...

Substituent Effects in CH Hydrogen Bond Interactions: Linear Free Energy Relationships and Influence of Anions

Blakely W. Tresca, Ryan J. Hansen, Calvin V. Chau, Benjamin P. Hay, Lev N. Zakharov, Michael M. Haley & Darren W. Johnson

Selective Recognition of Highly Hydrophilic Molecules in Water by Endo-Functionalized Molecular Tubes

Guo-Bao Huang, Sheng-Hua Wang, Hua Ke, Liu-Pan Yang & Wei Jiang
Selective recognition of neutral hydrophilic molecules in water is a challenge for supramolecular chemistry but commonplace in nature. By mimicking the binding pocket of natural receptors, endo-functionalized molecular tubes are proposed to meet this challenge. We found that two molecular tubes with inwardly directed hydrogen-bond donors recognize highly hydrophilic solvent molecules in water with high selectivity. In the complexes, hydrogen bonding occurs in the deep and hydrophobic cavity. The cooperative action between hydrogen bonding and...

Cyclodextrin-assisted modulation of the photophysical properties and acidity constant of pyrene-armed calix[4]arene

Jyotirmayee Mohanty, V. S. Kalyani & D. D. Malkhede
The supramolecular pKa shift and modulation in the monomer and excimer emission behaviour of pyrene-armed calixarene with cyclodextrins find applications in ratiometric sensing.

Bambusuril as a One-Electron Donor for Photoinduced Electron Transfer to Methyl Viologen in Mixed Crystals

Vladimir Sindelar, Lucie Ludvíková, Michal Babiak, Petr Klán, Dominik Heger, Tomas Fiala, Jan Švec, Tomáš Slanina, L’ubica Vetráková, Marek Nečas & Petr Kulhánek
Methyl viologen hexafluorophosphate (MV2+·2PF6–) and dodecamethylbambus[6]uril (BU6) form crystals in which the layers of viologen dications alternate with those of a 1:2 supramolecular complex of BU6 and PF6–. This arrangement allows for a one-electron reduction of MV2+ ions upon UV irradiation to form MV+• radical cations within the crystal structure with half-lives of several hours in air. The mechanism of this photoinduced electron transfer in the solid state and the origin of the long-lived charge-separated...

Hypervalent Iodine Based Reversible Covalent Bond in Rotaxane Synthesis

Vladimir Sindelar, Václav Havel, Marek Nečas, Markéta Kandrnálová & Zoran Kokan
The interlocked bambusuril: Reactive hypervalent iodine species possessing dynamic covalent bonds are utilized in a constitutive sense for the near quantitative synthesis of rotaxanes via the stabili...

Cucurbit[7]uril inclusion complexation as a supramolecular strategy for color stabilization of anthocyanin model compounds

Barbara Held, Hao Tang, Palani Natarajan, Cassio Pacheco da Silva, Volnir de Oliveira Silva, Cornelia Bohne & Frank H. Quina
Complete stabilization of the color of a flavylium cation by the formation of a higher order (1 : 2) complex with cucurbit[7]uril.

On the Nature of Guest Complexation in Water: Triggered Wetting–Water-Mediated Binding

Paolo Suating, Nicholas Ernst, Busayo Alagbe, Hannah Skinner, Joel Mague, Henry Ashbaugh & Bruce C. Gibb
TEEtOA vs. TEMOA – SAMPL8 dataset

Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution

Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lookene, Hans J. Reich, Kari Rissanen & Riina Aav
Chiral (all-R)-cyclohexanohemicucurbit[8]uril binds anions in a 1 : 1 ratio in pure methanol like a molecular Pac-Man™ with remarkable selectivity based on the size, shape and charge distribution of the anion.

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