Non-salen coumarin Schiff base chiral fluorescent probe turn on circularly polarized luminescence by Mg2+ and Zn2

In this work, we designed two non-salen coumarin Schiff base chiral fluorescent probes 3,3′-((1E,1′E)-(((1,2)-cyclohexane-1,2-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(7-methoxy-2H-chromen-2-one) (L1) and 3,3′-((1E,1′E)-(((1,2)-cyclohexane-1,2-diyl)bis(azaneylylidene))bis-(methaneylylidene)...

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Bibliographic Details
Published in:New journal of chemistry 2022-01, Vol.46 (11), p.5034-5042
Main Authors: Fu, Fubin, Zhang, Xueyan, Zhou, Shengquan, Shi, Wei, Li, Jiangmin, Yu, Jiajia, Rao, Yanzhao, Wu, Lei, Cao, Jing
Format: Article
Language:eng ; jpn
Subjects:
Circular polarization
Coumarin
Cyclohexane
Electron transfer
Enantiomers
Ethylenediaminetetraacetic acids
Fluorescent indicators
Imines
Ion probes
Luminescence
Recognition
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Summary:In this work, we designed two non-salen coumarin Schiff base chiral fluorescent probes 3,3′-((1E,1′E)-(((1,2)-cyclohexane-1,2-diyl)bis(azaneylylidene))bis(methaneylylidene))bis(7-methoxy-2H-chromen-2-one) (L1) and 3,3′-((1E,1′E)-(((1,2)-cyclohexane-1,2-diyl)bis(azaneylylidene))bis-(methaneylylidene))bis(2H-chromen-2-one) (L2), which have outstanding circular dichroic CD signals but almost show no circularly polarized luminescence (CPL) signals. By adding metal ions that can effectively inhibit photo-induced electron transfer (PET), it was observed that L1 can be used as a highly sensitive dual detection ion probe for Mg2+ and Zn2+ as Mg2+ and Zn2+ can turn on the CPL emission of L1. Moreover, (S,S)-L1 has exquisite recognition ability for the enantiomer of the chiral drug d/l-camphorsulfonate and showed reversible fluorescence “on/off” response with Zn2+ and EDTA. It was also found that L2 manifested selective recognition ability for Zn2+.
ISSN:1144-0546
1369-9261
DOI:10.1039/d1nj05817g