Related Experiment Video
Updated: Jul 15, 2025
06:44
From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
69.1K
Exploiting the Catenane Mechanical Bond Effect for Selective Halide Anion Transmembrane Transport
Hui Min Tay1, Toby G Johnson1, Andrew Docker1
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
Angewandte Chemie (International Ed. in English)
|September 29, 2023
Summary
Researchers developed novel neutral halogen bonding [2]catenanes for selective anion transport. These catenanes show enhanced binding and transport selectivity for halides over oxoanions, outperforming existing anionophores.
Area of Science:
- Supramolecular Chemistry
- Chemical Biology
- Materials Science
Background:
- Developing selective anion transporters is crucial for biological and therapeutic applications.
- Mechanical bonds, like those in catenanes, offer unique properties for molecular recognition.
- Halogen bonding (XB) is an emerging non-covalent interaction for anion binding.
Purpose of the Study:
- To synthesize and characterize novel neutral halogen bonding [2]catenanes.
- To investigate the anion binding and transport properties of these catenanes.
- To evaluate the role of the mechanical bond in enhancing anion selectivity.
Main Methods:
- Template-directed synthesis of [2]catenanes using chloride ions.
- Anion binding studies in aqueous-organic media.
- Transmembrane anion transport assays using large unilamellar vesicles (LUVs).
Main Results:
- Successfully synthesized neutral halogen bonding [2]catenanes with high yields.
- Demonstrated strong halide selectivity over oxoanions, with enhanced binding affinities compared to macrocyclic precursors.
- Achieved superior transmembrane transport selectivity for chloride over hydroxide and nitrate, outperforming existing acyclic XB anionophores.
Conclusions:
- Neutral halogen bonding [2]catenanes are effective and selective anion transporters.
- The mechanical bond in catenanes significantly enhances anion transport selectivity.
- These findings pave the way for new therapeutic anionophores.
More Related Videos
Related Concept Videos
02:46Halogenation of Alkenes
15.8K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
15.8K
02:45Alkyl Halides
16.9K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
16.9K
02:38Electrophilic Addition to Alkynes: Halogenation
8.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.3K
02:17Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule
14.3K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.3K
01:17Pore Transport and Ion-Pair Transport
494
Pore transport and ion-pair formation are critical mechanisms for the absorption and distribution of drugs in the body.
Pore transport, also known as convective transport, is a process where small molecules like urea, water, and sugars rapidly cross cell membranes as though there were channels or pores in the membrane. Although direct microscopic evidence is limited but the concept of pores or channels is widely accepted based on physiological evidence. Despite the lack of direct...
Pore transport, also known as convective transport, is a process where small molecules like urea, water, and sugars rapidly cross cell membranes as though there were channels or pores in the membrane. Although direct microscopic evidence is limited but the concept of pores or channels is widely accepted based on physiological evidence. Despite the lack of direct...
494
02:26SN2 Reaction: Transition State
9.9K
An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
9.9K