Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

Mondal, Pravat; Solel, Ephrath; Mitra, Shubhanjan; Keinan, Ehud; Reany, Ofer

doi:10.1021/acs.orglett.9b04166

Cited by 13 publications

(7 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…During the following years, different reaction conditions for the preparation of bambusurils were investigated, including the use of various organic solvents and applying conventional as well as microwave heating. , The majority of the bambusurils reported so far consist of six identical 2,4-disubstituted glycoluril units. Exceptions are semithio- and semiaza-bambusurils, made of 3-thio- and 3-azaglycolurils, − and chiral bambusurils, having different substituents in the 2,4-positions of the glycolurils. − Moreover, recently, we reported the synthesis of the first monofunctionalized bambusuril using a statistically driven condensation of two different glycolurils . Bambusuril properties such as solubility, lipophilicity, and binding affinity toward anions could be significantly influenced by the type of substituents on their portals.…”

Section: Introductionmentioning

confidence: 99%

Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction

et al. 2022

View full text Add to dashboard Cite

Bambusurils are macrocyclic molecules that are known for their high binding affinity and selectivity toward anions. Here, we present the preparation of two bambusurils bearing fluorinated substituents and one carboxylic function. These monofunctionalized bambusurils were conjugated with crown ether and cholesterol units. The resulting conjugates were successfully tested in liquid–liquid extraction of inorganic salts and chloride/bicarbonate transport across lipid bilayers.

show abstract

Section: Introductionmentioning

confidence: 99%

Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction

et al. 2022

View full text Add to dashboard Cite

show abstract

“…24−26 Accordingly, the Recently, four intramolecular distances, d 1 −d 4 , and a torsional angle, θ (vide infra), were defined to characterize the conformations of the various heteroisomers of BU [4]. 27 Accordingly, d 1 is the distance between the peripheral carbonyl heteroatoms, d 2 is the distance between the C 2 symmetryrelated methine carbon atoms, d 3 is the distance between the two equatorial carbonyl oxygen atoms (on the same side), and d 4 is the distance between the planes that include all four methine groups of each portal (Figure 4B). In addition, each glycoluril can be viewed as two rigid flaps fused together at an angle of 113°: one flap participates in the molecular portal, whereas the other flap constitutes the molecular equator.…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

Inherently Chiral Bambus[4]urils

Mohite

Reany

2020

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

A new class of bambus [4]urils (BU[4]s) composed of asymmetric N,N′-disubstituted glycoluril subunits with different alkyl groups were designed, synthesized, and fully characterized by NMR techniques and X-ray crystallography. Structural studies showed that four macrocyclic diastereoisomers are possible: two S n symmetric achiral macrocycles and two macrocycles that are "inherently" chiral. The relative "head-to-tail" arrangement of the N-substituents in Bn 4 Me 4 BU[4], 5a, clearly observed by X-ray spectroscopy analysis, determines the overall symmetry of the bambusuril structure. Chiral Pr 4 Me 4 BU[4], 4b, was resolved by chiral high-performance liquid chromatography (HPLC) into its enantiomers, and all four inherently chiral bambusuril pairs (two Pr 4 Me 4 BU[4] and two Bn 4 Me 4 BU[4] stereoisomers, 4b, 4d, 5b, and 5d) were clearly observed by 1 H NMR spectroscopy with the aid of (R)-BINOL as a chiral solvating agent. This latter methodology provides a rapid and powerful approach for investigating the enantiopurity of inherently chiral cavitands, which complements and augments the conventional chromatographic approaches.

show abstract

“…Furthermore, replacing their portal ureido oxygen atoms with either sulfur or nitrogen produced various hetero ‐BU[6] molecules, such as semithio ‐BU[6] or semiaza ‐BU[6]s [37] . These new variants exhibited variable binding modes, [38–41] demonstrating channel‐like, multiple anions binding, [41] and efficient transmembrane chloride transport [42,43] . Sindelar and co‐workers have recently demonstrated the ionophore behavior of dodecabenzyl‐bambus[6]uril (Bn 12 BU[6]) embedded within a conducting polymer (PEDOT) in a solid‐contact ion selective electrode (SC‐ISE) and employed it to determine perchlorate concentrations at a μM level [44] .…”

Section: Introductionmentioning

confidence: 99%

Selective Perchlorate Sensing Using Electrochemical Impedance Spectroscopy with Self‐Assembled Monolayers of semiaza‐Bambusurils

Khurana,

Alami,

Nijhuis

et al. 2023

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

In the last two decades, perchlorate salts have been identified as environmental pollutants and recognized as potential substances affecting human health. We describe self‐assembled monolayers (SAMs) of novel semiaza‐bambus[6]urils (semiaza‐BUs) equipped with thioethers or disulfide (dithiolane) functionalities as surface‐anchoring groups on gold electrodes. Cyclic voltammetry (CV) with Fe(CN)63‐/4‐ as a redox probe, together with X‐ray photoelectron spectroscopy (XPS), atomic force microscopy (AFM) and ellipsometry, were employed to characterize the interactions at the interface between the anchoring groups and the metal substrate. Data showed that the anion receptors' packing on the gold strongly depends on the anchoring group. As a result, SAMs of BUs with lipoic amide side chains show a concentration‐dependent layer thickness. The BU SAMs are extremely stable on repeated electrochemical potential scans and can selectively recognize perchlorate anions. Our electrochemical impedance spectroscopy (EIS) studies indicated that semiaza‐BU equipped with the lipoic amide side chains binds perchlorate (2‐100 mM) preferentially over other anions such as F‐, Cl‐, I‐, AcO‐, H2PO4‐, HPO42‐, SO42‐, NO2‐, NO3‐, or CO32‐. The resistance performance is 10 to 100 times more efficient than SAMs containing all other tested anions.

show abstract

Equatorial Sulfur Atoms in Bambusurils Spawn Cavity Collapse

Cited by 13 publications

References 16 publications

Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction

Monofunctionalized Fluorinated Bambusurils and Their Conjugates for Anion Transport and Extraction

Inherently Chiral Bambus[4]urils

Selective Perchlorate Sensing Using Electrochemical Impedance Spectroscopy with Self‐Assembled Monolayers of semiaza‐Bambusurils

Contact Info

Product

Resources

About