A Photoexcitation‐Induced Twisted Intramolecular Charge Shuttle

Charge transfer and separation are important processes governing numerous chemical reactions. Fundamental understanding of these processes and the underlying mechanisms is critical for photochemistry. Herein, we report the discovery of a new charge‐transfer and separation process, namely the twisted...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-05, Vol.58 (21), p.7073-7077
Main Authors: Chi, Weijie, Qiao, Qinglong, Lee, Richmond, Liu, Wenjuan, Teo, Yock Siong, Gu, Danning, Lang, Matthew John, Chang, Young‐Tae, Xu, Zhaochao, Liu, Xiaogang
Format: Article
Language:English
Subjects:
Biomolecules
biosensors
Charge transfer
charge transfer and separation
Chemical compounds
Chemical reactions
Coumarin
donor–acceptor systems
Fluorescent indicators
fluorescent probes
fluorophore
Fluorophores
Organic chemistry
Photochemistry
Photoexcitation
Probes
Rhodamine
Separation
Viscosity
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Summary:Charge transfer and separation are important processes governing numerous chemical reactions. Fundamental understanding of these processes and the underlying mechanisms is critical for photochemistry. Herein, we report the discovery of a new charge‐transfer and separation process, namely the twisted intramolecular charge shuttle (TICS). In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state because of an approximately 90° intramolecular rotation. TICS systems thus exhibit charge shuttling. TICSs exist in several chemical families of fluorophores (such as coumarin, BODIPY, and oxygen/carbon/silicon–rhodamine), and could be utilized to construct functional fluorescent probes (i.e., viscosity‐ or biomolecule‐sensing probes). The discovery of the TICS process expands the current perspectives of charge‐transfer processes and will inspire future applications. Twisted intramolecular charge shuttle (TICS): In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state due to an approximately 90° intramolecular rotation that is induced upon photoexcitation. This results in charge shuttling. TICSs exist in several families of fluorophores and could be utilized in the construction of fluorescent probes.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201902766