Kinetic Trapping of an Out‐of‐Equilibrium Dynamic Library of Imines by Changing Solvent

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(37)

Published: April 8, 2024

A well-behaved dynamic library composed of two imines and corresponding amines was subjected to the action an activated carboxylic acid (ACA), whose decarboxylation is known be base promoted, in different solvents, namely CD

Language: Английский

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Divergent Synthesis of Chiroptical Molecular Switches Based on 1,2-Diaxial Atropisomers

JACS Au, Journal Year: 2024, Volume and Issue: 4(11), P. 4445 - 4454

Published: Oct. 14, 2024

The development of chiroptical molecular switches for chiral sensing, data communication, optical displays, logic gates, and asymmetric catalysis is currently a vibrant frontier science technology. Herein, we report practical artificial dynamic system based on 1,2-diaxial atropisomer. Organocatalytic parallel kinetic resolution allows the divergent synthesis two sets stereoisomers with vicinal C-C N-N axes from same racemic single-axis substrates. By simply varying configuration single catalyst, all four are accessible. successive conduction covalent unlocking/locking thermal-isomerization processes enables sequential switching between atropisomeric states electronic circular dichroism signal reversal, providing an example multistate switches.

Language: Английский

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Non‐Equilibrium Kinetic States of a [2]Rotaxane‐Based Molecular Shuttle Controlled by Acid Concentrations

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(50)

Published: Oct. 17, 2022

A [2]rotaxane-based molecular shuttle with an acid-responsive asymmetric macrocycle on a symmetric dumbbell axle is reported. Upon adding TFA, the macrocycle, namely amine naphthotube, protonated and translocates from di(quaternary ammonium) station to triazole stations because of electrostatic repulsion weakened binding. The shuttling kinetics are slow due steric hindrance caused by ethyl group quaternary ammonium center can be followed 1 H NMR spectroscopy. Interestingly, it was found that depends concentration TFA. kinetic intermediate detected even captured in presence high Extensive control experiments revealed capture related different protonation states rotaxanes.

Language: Английский

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Atropselective Organocatalytic Synthesis of Chiral Compounds Containing Nitrogen along the Axis of Chirality

Symmetry, Journal Year: 2023, Volume and Issue: 15(6), P. 1261 - 1261

Published: June 15, 2023

Atropisomers, i.e., stereoisomers that are distinct because their free rotation about a single bond is hindered by steric interactions between nearby bulky groups or electrostatics, may interact with surroundings in different ways, and also exhibit properties. They be found as natural products, pharmaceutical agricultural active ingredients, chiral ligands organocatalysts, functional materials. Our ability to synthesize them stereoselectively sustainable way, using achiral materials simply the aid of an organocatalyst mild conditions, has become hot topic research. This review provides overview recent achievements synthesis atropisomers containing C-N N-N axes chirality.

Language: Английский

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Transient co-assemblies of micron-scale colloids regulated by ATP-fueled reaction networks

Chemical Science, Journal Year: 2023, Volume and Issue: 14(43), P. 12299 - 12307

Published: Jan. 1, 2023

An ATP-fueled DNA based enzymatic reaction network regulates transient co-assemblies of micron-scale colloids. The system produces minimal waste, shows ATP-dependent behavior, and can be reactivated for up to three consecutive cycles.

Language: Английский

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