Supramolecular recognition and mechanically interlocked molecules based on imidazoliums and crown ethers DOI

Houyang Xu,

Kelong Zhu

Scientia Sinica Chimica, Journal Year: 2023, Volume and Issue: unknown

Published: Sept. 26, 2023

Language: Английский

Supramolecular and molecular capsules, cages and containers DOI Creative Commons

C. Cox,

Jessica Hale,

Paulina Molinska

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(21), P. 10380 - 10408

Published: Jan. 1, 2024

Stemming from early seminal notions of molecular recognition and encapsulation, three-dimensional, cavity-containing capsular compounds assemblies have attracted intense interest due to the ability modulate chemical physical properties species encapsulated within these confined spaces compared bulk environments. With such a diverse range covalent motifs non-covalent (supramolecular) interactions available assemble building blocks, an incredibly wide-range capsular-type architectures been developed. Furthermore, synthetic tunability internal environments gives chemists opportunity engineer systems for uses in sensing, sequestration, catalysis transport molecules, just name few. In this tutorial review, overview is provided into design principles, synthesis, characterisation, structural facets coordination cages, porous organic supramolecular capsules, foldamers mechanically interlocked molecules. Using recent examples, advantages limitations each system are explored, highlighting their application various tasks functions.

Language: Английский

Citations

13

A Modular Strategy for the Synthesis of Macrocycles and Medium-Sized Rings via Cyclization/Ring Expansion Cascade Reactions DOI Creative Commons

Illya Zalessky,

Jack M. Wootton, Jerry K. F. Tam

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(8), P. 5702 - 5711

Published: Feb. 19, 2024

Macrocycles and medium-sized rings are important in many scientific fields technologies but hard to make using current methods, especially on a large scale. Outlined herein is strategy by which functionalized macrocycles can be prepared cyclization/ring expansion (CRE) cascade reactions, without resorting high dilution conditions. CRE reactions designed operate exclusively via kinetically favorable 5–7-membered ring cyclization steps; this means that the problems typically associated with classical end-to-end macrocyclization avoided. A modular synthetic approach has been developed facilitate simple assembly of requisite linear precursors, then converted into an extremely broad range one nine protocols.

Language: Английский

Citations

11

A crown-ether-enabled eutectic electrolyte for ultra-high temperature lithium metal batteries DOI

Yulai Pu,

Qin Wang,

Renju Dou

et al.

Energy storage materials, Journal Year: 2024, Volume and Issue: 67, P. 103285 - 103285

Published: Feb. 20, 2024

Language: Английский

Citations

8

Active template synthesis DOI Creative Commons
Romain Jamagne, M. Power, Zhi‐Hui Zhang

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The active template synthesis of rotaxanes, catenanes and knots exploits the dual ability metals, or particular arrangements functional groups, to serve as both a catalyst assemble covalently capture interlocked molecules.

Language: Английский

Citations

8

A Platform Approach to Cleavable Macrocycles for the Controlled Disassembly of Mechanically Caged Molecules DOI Creative Commons
Abed Saady, Georgia K. Malcolm,

Matthew P. Fitzpatrick

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(16)

Published: Jan. 26, 2024

Abstract Inspired by interlocked oligonucleotides, peptides and knotted proteins, synthetic systems where a macrocycle cages bioactive species that is “switched on” breaking the mechanical bond have been reported. However, to date, each example uses bespoke chemical design. Here we present platform approach mechanically caged structures wherein single precursor diversified at late stage include range of trigger units control ring opening in response enzymatic, chemical, or photochemical stimuli. We also demonstrate our applicable other classes macrocycles suitable for rotaxane catenane formation.

Language: Английский

Citations

6

Molecular entanglement can strongly increase basicity DOI Creative Commons
Giorgio Capocasa, Federico Frateloreto, Matteo Valentini

et al.

Communications Chemistry, Journal Year: 2024, Volume and Issue: 7(1)

Published: May 28, 2024

Brønsted basicity is a fundamental chemical property featured by several kinds of inorganic and organic compounds. In this Review, we treat particularly high resulting from the mechanical entanglement involving two or more molecular subunits in catenanes rotaxanes. Such allows number basic sites to be close proximity with each other, highly increasing proton affinity comparison corresponding, non-entangled counterparts up obtain superbases, properly defined as mechanically interlocked superbases. following pages, development kind superbases will described historical perusal, starting initial, serendipitous findings most recent reports where strong entangled units object rational design.

Language: Английский

Citations

3

Skeletal Editing of Mechanically Interlocked Molecules: Nitrogen Atom Deletion from Crown Ether-Dibenzylammonium Rotaxanes DOI Creative Commons
Maxime Gauthier, Jessica B. M. Whittingham, Avantika Hasija

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(43), P. 29496 - 29502

Published: Oct. 21, 2024

Removing the nitrogen atom from secondary amines while simultaneously linking remaining fragments is a powerful form of late-stage skeletal editing. Here, we report its use for deletion dibenzylammonium template used to assemble crown ether rotaxanes. The reaction uses an anomeric amide that activates generate carbon-carbon bond replaces amine nitrogen. Despite potential dethreading intermediate diradical pair, was successfully deleted series rotaxane axles as long macrocycle could access coconformations did not inhibit group. skeletally edited interlocked molecules were obtained directly parent ether-dibenzylammonium rotaxanes in modest yields (23-36%) and characterized by NMR spectroscopy, mass spectrometry, X-ray crystallography. One shows network weak CH···O hydrogen bonds between benzylic methylene groups axle solid state, place ether-ammonium binding motif parent, unedited, rotaxane.

Language: Английский

Citations

3

Pseudo[3]rotaxane and [3]Rotaxane of Per(5-carboxy-5-dehydroxymethyl)-Cyclodextrins Utilizing Carboxylic Acid Dimer as Recognition Units DOI
Takashi Nakamura,

Masamune Kuwabara,

Haoyang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(10), P. 3603 - 3609

Published: March 5, 2025

The formation of pseudo[3]rotaxane using dimers per(5-carboxy-5-dehydroxymethyl)-cyclodextrins as ring components and secondary ammoniums an axle is presented. This supramolecule formed by the unique interaction circularly arranged carboxylic acid acting hydrogen bonding acceptors covering moiety. On these grounds, we could achieve synthesis [3]rotaxane capping terminal groups through thiol-ene reactions.

Language: Английский

Citations

0

A Biocompatible Deep Eutectic Electrolyte Enables Ultra‐Fast Charging in Lithium‐Ion Batteries DOI Open Access
Xiaoyan Ren,

Renju Dou,

Qin Wang

et al.

Advanced Functional Materials, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Abstract Lithium‐ion batteries are of great significance in improving people's lives by offering reliable, long‐lasting, and high‐capacity power solutions. However, safety concerns, particularly those related to electrolyte leakage under harsh conditions, pose significant obstacles their practical applications. In this context, a biocompatible deep eutectic (DEE) is presented formulated blending 2,6‐dimethylpyrazine (DMPY)—a natural ingredient approved the World Health Organization (WHO) due its origin—with lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) specific molar ratios. Benefitting from abundant N atoms, DMPY molecule effectively drives Li─N coordination with Li + cations, forms hydrogen bonds TFSI − anions, consequently enhances dissociation LiTFSI—all which trigger formation DEE. This DEE solution demonstrates remarkable performance characteristics, including high transference number (0.67), substantial ion conductivity (0.57 mS cm −1 at 30 °C), moderate oxidation voltage (4.10 V vs Li/Li ). These attributes complemented interface stability long‐term cycling across broad range rates, notably rate 10 C, ascribed generation robust organic–inorganic gradient solid‐electrolyte interphase. work opens intriguing perspectives design novel electrolytes for demanded lithium‐ion while ensuring good biocompatibility.

Language: Английский

Citations

0

A Thiourea-Based Rotaxane Catalyst: Nucleophilic Fluorination Phase-Transfer Process Unlocked by the Mechanical Bond DOI
Julio Puigcerver, Juan S. Dato-Santiago, Mateo Alajarı́n

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 18, 2025

We report a five-component clipping approach using activated isophthaloyl-derived esters to synthesize an amide-based thiourea rotaxane. This method overcomes acyl chloride limitations with nucleophilic threads. The steric hindrance of the mechanical bond enables, for first time, interlocked as hydrogen-bonding phase-transfer organocatalyst in fluorinations. highlights how bonds expand catalysis processes previously incompatible conventional catalysts.

Language: Английский

Citations

0