Non‐Equilibrium Kinetic States of a [2]Rotaxane‐Based Molecular Shuttle Controlled by Acid Concentrations
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 the amine naphthotube, is protonated and translocates from the di(quaternary ammonium) station to the triazole stations because of ele...
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| Published in | Angewandte Chemie International Edition Vol. 61; no. 50; pp. e202214296 - n/a |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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Wiley
12.12.2022
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| Edition | International ed. in English |
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| Abstract | 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 the amine naphthotube, is protonated and translocates from the di(quaternary ammonium) station to the triazole stations because of electrostatic repulsion and weakened binding. The shuttling kinetics are slow due to the steric hindrance caused by the ethyl group on the quaternary ammonium center and can be followed by 1H NMR spectroscopy. Interestingly, it was found that the shuttling kinetics depends on the concentration of TFA. A kinetic intermediate was detected and can even be captured in the presence of a high concentration of TFA. Extensive control experiments revealed that the shuttling kinetics and the capture of the kinetic intermediate are related to the different protonation states of the rotaxanes.
A [2]rotaxane‐based molecular shuttle with an acid‐responsive asymmetric macrocycle on a symmetric dumbbell axle has been synthesized. The shuttling kinetics can be controlled by the acid concentration and the kinetic intermediate can even be captured at a high concentration of acid. This was explained by invoking different protonation states of the rotaxane at different concentrations of acid. |
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| AbstractList | 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 the amine naphthotube, is protonated and translocates from the di(quaternary ammonium) station to the triazole stations because of electrostatic repulsion and weakened binding. The shuttling kinetics are slow due to the steric hindrance caused by the ethyl group on the quaternary ammonium center and can be followed by H-1 NMR spectroscopy. Interestingly, it was found that the shuttling kinetics depends on the concentration of TFA. A kinetic intermediate was detected and can even be captured in the presence of a high concentration of TFA. Extensive control experiments revealed that the shuttling kinetics and the capture of the kinetic intermediate are related to the different protonation states of the rotaxanes. 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 the amine naphthotube, is protonated and translocates from the di(quaternary ammonium) station to the triazole stations because of electrostatic repulsion and weakened binding. The shuttling kinetics are slow due to the steric hindrance caused by the ethyl group on the quaternary ammonium center and can be followed by H NMR spectroscopy. Interestingly, it was found that the shuttling kinetics depends on the concentration of TFA. A kinetic intermediate was detected and can even be captured in the presence of a high concentration of TFA. Extensive control experiments revealed that the shuttling kinetics and the capture of the kinetic intermediate are related to the different protonation states of the rotaxanes. 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 the amine naphthotube, is protonated and translocates from the di(quaternary ammonium) station to the triazole stations because of electrostatic repulsion and weakened binding. The shuttling kinetics are slow due to the steric hindrance caused by the ethyl group on the quaternary ammonium center and can be followed by 1H NMR spectroscopy. Interestingly, it was found that the shuttling kinetics depends on the concentration of TFA. A kinetic intermediate was detected and can even be captured in the presence of a high concentration of TFA. Extensive control experiments revealed that the shuttling kinetics and the capture of the kinetic intermediate are related to the different protonation states of the rotaxanes. A [2]rotaxane‐based molecular shuttle with an acid‐responsive asymmetric macrocycle on a symmetric dumbbell axle has been synthesized. The shuttling kinetics can be controlled by the acid concentration and the kinetic intermediate can even be captured at a high concentration of acid. This was explained by invoking different protonation states of the rotaxane at different concentrations of acid. 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 the amine naphthotube, is protonated and translocates from the di(quaternary ammonium) station to the triazole stations because of electrostatic repulsion and weakened binding. The shuttling kinetics are slow due to the steric hindrance caused by the ethyl group on the quaternary ammonium center and can be followed by 1 H NMR spectroscopy. Interestingly, it was found that the shuttling kinetics depends on the concentration of TFA. A kinetic intermediate was detected and can even be captured in the presence of a high concentration of TFA. Extensive control experiments revealed that the shuttling kinetics and the capture of the kinetic intermediate are related to the different protonation states of the rotaxanes. 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 the amine naphthotube, is protonated and translocates from the di(quaternary ammonium) station to the triazole stations because of electrostatic repulsion and weakened binding. The shuttling kinetics are slow due to the steric hindrance caused by the ethyl group on the quaternary ammonium center and can be followed by 1H NMR spectroscopy. Interestingly, it was found that the shuttling kinetics depends on the concentration of TFA. A kinetic intermediate was detected and can even be captured in the presence of a high concentration of TFA. Extensive control experiments revealed that the shuttling kinetics and the capture of the kinetic intermediate are related to the different protonation states of the rotaxanes. |
| Author | Zhao, Lei‐Min Zheng, Li‐Shuo Jiang, Wei Wang, Xiaoping |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/36251219$$D View this record in MEDLINE/PubMed |
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| Keywords | ROTATION Non-Equilibrium State Kinetics DRIVEN MOTORS ROTARY Molecular Shuttle Naphthotube Rotaxane |
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| Snippet | A [2]rotaxane‐based molecular shuttle with an acid‐responsive asymmetric macrocycle on a symmetric dumbbell axle is reported. Upon adding TFA, the macrocycle,... A [2]rotaxane-based molecular shuttle with an acid-responsive asymmetric macrocycle on a symmetric dumbbell axle is reported. Upon adding TFA, the macrocycle,... |
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| SubjectTerms | Ammonium Ammonium Compounds Antifungal agents Chemistry Chemistry, Multidisciplinary Kinetics Magnetic Resonance Spectroscopy Molecular Shuttle Naphthotube NMR NMR spectroscopy Non-Equilibrium State Nuclear magnetic resonance Physical Sciences Protonation Rotaxane Rotaxanes Rotaxanes - chemistry Science & Technology Steric hindrance Triazoles - chemistry |
| Title | Non‐Equilibrium Kinetic States of a [2]Rotaxane‐Based Molecular Shuttle Controlled by Acid Concentrations |
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