Improving the quantum yields of fluorophores by inhibiting twisted intramolecular charge transfer using electron-withdrawing group-functionalized piperidine auxochromes

Herein, we present that the negative inductive effect exerted by electron-withdrawing groups, such as sulfone groups, can obviously improve the ionization potential of amino auxochromes, thereby effectively inhibiting twisted intramolecular charge transfer (TICT) and markedly improving the quantum y...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-01, Vol.56 (5), p.715-718
Main Authors: Lv, Xin, Gao, Chunmei, Han, Taihe, Shi, Hu, Guo, Wei
Format: Article
Language:English
Subjects:
Aqueous solutions
Charge transfer
Chemical compounds
Fluorescence
Ionization potentials
NMR
Nuclear magnetic resonance
Piperidine
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Summary:Herein, we present that the negative inductive effect exerted by electron-withdrawing groups, such as sulfone groups, can obviously improve the ionization potential of amino auxochromes, thereby effectively inhibiting twisted intramolecular charge transfer (TICT) and markedly improving the quantum yields of several families of fluorophores in aqueous solution. Using sulfone-functionalized piperdine as an auxochrome, the quantum yields of rhodamine and its red to NIR derivatives in aqueous solution have substantially been improved.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc09138f