Visible‐Light‐Switchable Tellurium‐Based Chalcogen Bonding: Photocontrolled Anion Binding and Anion Abstraction Catalysis

Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self‐assembly systems and materials. Herein, for the first time, we demonstrate a unique visible‐light‐switchable telluro‐tria...

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Published inAngewandte Chemie International Edition Vol. 62; no. 5; pp. e202212707 - n/a
Main Authors Duan, Hong‐Ying, Han, Shi‐Tao, Zhan, Tian‐Guang, Liu, Li‐Juan, Zhang, Kang‐Da
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 26.01.2023
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Affinity
Alkylation
Anion Binding
Anions
Antifungal agents
Azo compounds
Azobenzene
Binding
Bonding
Catalysis
Chalcogen Bonding
Chalcogen bonds
Chemistry
Chemistry, Multidisciplinary
Irradiation
Photoswitch
Physical Sciences
Radiation
Receptors
Science & Technology
Supramolecular Catalysis
Tellurium
Wavelengths
Anion Binding
Chalcogen Bonding
TRANSPORT
Supramolecular Catalysis
Photoswitch
Azobenzene
Online AccessGet full text
ISSN1433-7851
1521-3773
1521-3773
DOI10.1002/anie.202212707

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Abstract Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self‐assembly systems and materials. Herein, for the first time, we demonstrate a unique visible‐light‐switchable telluro‐triazole/triazolium‐based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo‐derived ChB receptors and the halide anions (Cl−, Br−) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis‐bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans‐monodentate receptors. In particular, the telluro‐triazolium‐based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB‐assisted halide ion in a Friedel–Crafts alkylation benchmark reaction. A visible‐light‐switchable telluro‐triazolium‐based chalcogen bonding receptor has been constructed in which the Te moieties are connected by azobenzene cores. The receptor shows photocontrolled halide anion binding and acts as a photocontrolled organocatalyst for chalcogen‐bonding‐assisted halide anion ion in a Friedel–Crafts reaction.
AbstractList Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self-assembly systems and materials. Herein, for the first time, we demonstrate a unique visible-light-switchable telluro-triazole/triazolium-based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo-derived ChB receptors and the halide anions (Cl-, Br-) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis-bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans-monodentate receptors. In particular, the telluro-triazolium-based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB-assisted halide abstraction in a Friedel-Crafts alkylation benchmark reaction.
Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self‐assembly systems and materials. Herein, for the first time, we demonstrate a unique visible‐light‐switchable telluro‐triazole/triazolium‐based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo‐derived ChB receptors and the halide anions (Cl − , Br − ) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis ‐bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans ‐monodentate receptors. In particular, the telluro‐triazolium‐based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB‐assisted halide abstraction in a Friedel–Crafts alkylation benchmark reaction.
Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self‐assembly systems and materials. Herein, for the first time, we demonstrate a unique visible‐light‐switchable telluro‐triazole/triazolium‐based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo‐derived ChB receptors and the halide anions (Cl−, Br−) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis‐bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans‐monodentate receptors. In particular, the telluro‐triazolium‐based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB‐assisted halide ion in a Friedel–Crafts alkylation benchmark reaction. A visible‐light‐switchable telluro‐triazolium‐based chalcogen bonding receptor has been constructed in which the Te moieties are connected by azobenzene cores. The receptor shows photocontrolled halide anion binding and acts as a photocontrolled organocatalyst for chalcogen‐bonding‐assisted halide anion ion in a Friedel–Crafts reaction.
Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self-assembly systems and materials. Herein, for the first time, we demonstrate a unique visible-light-switchable telluro-triazole/triazolium-based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo-derived ChB receptors and the halide anions (Cl- , Br- ) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis-bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans-monodentate receptors. In particular, the telluro-triazolium-based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB-assisted halide abstraction in a Friedel-Crafts alkylation benchmark reaction.Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self-assembly systems and materials. Herein, for the first time, we demonstrate a unique visible-light-switchable telluro-triazole/triazolium-based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo-derived ChB receptors and the halide anions (Cl- , Br- ) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis-bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans-monodentate receptors. In particular, the telluro-triazolium-based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB-assisted halide abstraction in a Friedel-Crafts alkylation benchmark reaction.
Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self‐assembly systems and materials. Herein, for the first time, we demonstrate a unique visible‐light‐switchable telluro‐triazole/triazolium‐based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo‐derived ChB receptors and the halide anions (Cl−, Br−) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis‐bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans‐monodentate receptors. In particular, the telluro‐triazolium‐based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB‐assisted halide abstraction in a Friedel–Crafts alkylation benchmark reaction.
Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of supramolecular self-assembly systems and materials. Herein, for the first time, we demonstrate a unique visible-light-switchable telluro-triazole/triazolium-based chalcogen bonding (ChB) system in which the Te moieties are connected by azobenzene cores. The binding strengths between these azo-derived ChB receptors and the halide anions (Cl , Br ) could be reversibly regulated upon irradiation by visible light of different wavelengths. The cis-bidentate ChB receptors exhibit enhanced halide anion binding ability compared to the trans-monodentate receptors. In particular, the telluro-triazolium-based ChB receptor can achieve both high and significantly photoswitchable binding affinities for halide anions, which enable it to serve as an efficient photocontrolled organocatalyst for ChB-assisted halide abstraction in a Friedel-Crafts alkylation benchmark reaction.
Author Liu, Li‐Juan
Han, Shi‐Tao
Zhang, Kang‐Da
Duan, Hong‐Ying
Zhan, Tian‐Guang
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  surname: Duan
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  givenname: Kang‐Da
  orcidid: 0000-0002-9183-8364
  surname: Zhang
  fullname: Zhang, Kang‐Da
  email: Kangda.Zhang@zjnu.cn
  organization: Zhejiang Normal University
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Keywords Anion Binding
Chalcogen Bonding
TRANSPORT
Supramolecular Catalysis
Photoswitch
Azobenzene
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  article-title: Catalysis with Chalcogen Bonds
  publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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Snippet Exploring new noncovalent bonding motifs with reversibly tunable binding affinity is of fundamental importance in manipulating the properties and functions of...
Source Web of Science
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StartPage e202212707
SubjectTerms Affinity
Alkylation
Anion Binding
Anions
Antifungal agents
Azo compounds
Azobenzene
Binding
Bonding
Catalysis
Chalcogen Bonding
Chalcogen bonds
Chemistry
Chemistry, Multidisciplinary
Irradiation
Photoswitch
Physical Sciences
Radiation
Receptors
Science & Technology
Supramolecular Catalysis
Tellurium
Wavelengths
Title Visible‐Light‐Switchable Tellurium‐Based Chalcogen Bonding: Photocontrolled Anion Binding and Anion Abstraction Catalysis
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202212707
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https://www.ncbi.nlm.nih.gov/pubmed/36383643
https://www.proquest.com/docview/2766927004
https://www.proquest.com/docview/2737464485
Volume 62
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