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Metal-coordination driven intramolecular twisting: A turn-on fluorescent-redox probe for Hg2+ ions through the interaction of ferrocene nonbonding orbitals and dibenzylidenehydrazine
Bijan Mondal
Published in Royal Society of Chemistry
2019
PMID: 31090757
Volume: 48
   
Issue: 23
Pages: 8209 - 8220
Abstract
A unique C2 symmetric azine bridged bi-ferrocenyl receptor (4) has been modelled and synthesized. In this work, we are able to synthetically regulate conjugation of the dibenzylidenehydrazine fluorophore unit to unexpectedly reveal metal-coordination driven intramolecular twisting. The present probe shows a dramatic turn-on fluorescence response with 91 fold increment of quantum yield along with 17 nm blue shift upon binding with Hg2+ ions selectively with a limit of detection as low as 15 nM. Upon Hg2+ recognition, the ferrocene/ferrocinium redox peak was anodically shifted by ΔE1/2 = 78 mV, indicating the formation of a new complex species. A plausible binding mode of Hg2+ ions with compound 4 has been proposed based on 1H NMR titration, a high-resolution mass spectrometry (HRMS) study and a density functional theory (DFT) study along with the Job's plot analysis. Interestingly, DFT calculations have revealed that the reason for fluorescence enhancement after coordination to Hg2+ ions is not due to conventional restricted CN isomerization or interrupted N-N single bond rotation rather it is due to the increase of the π ← π∗ transition at the expense of the n → π∗ (aromatic) transition of the free ligand. Furthermore, TD-DFT calculations of the first excited singlet state of 4 and [4·Hg2+] revealed the involvement of the aromatic π electrons with the vacant site of Hg2+ ions which may be further attributed to the fluorescence enhancement phenomenon. In addition, receptor 4 was successfully applied for the detection of Hg2+ ions in real samples. © 2019 The Royal Society of Chemistry.
About the journal
JournalData powered by TypesetDalton Transactions
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN14779226
Open AccessNo
Concepts (19)
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    Aromatic compounds
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    Binding energy
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    Blue shift
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    Excited states
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    Fluorescence
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    Ions
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    Iron compounds
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    Mass spectrometry
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    Organometallics
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    Probes
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    EXCITED SINGLET STATE
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    Fluorescence enhancement
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    High resolution mass spectrometry
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    INTRAMOLECULAR TWISTING
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    Limit of detection
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    METAL COORDINATION
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    NON-BONDING ORBITAL
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    Td-dft calculations
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    Density functional theory