Synthesis and fluorescent sensory properties of a 5-cyanostilbene derivative linked to monoaza-15-crown-5

Juin Meng Yu, Ching Yi Chen, Yun Chen

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

To study the effect of electron-withdrawing group upon sensory characteristics of fluorescent chemosensors containing crown ether moiety (monoaza-15-crown-5), two stilbene derivatives CN-Crown and H-Crown were synthesized to compare their selectivity and sensitivity toward metal ions. CN-Crown contains two e-withdrawing groups (bromine and cyano) in stilbene unit, whereas H-Crown possesses bromine only. Fluorescence spectral variations in the presence of different metal ions or concentrations were used to elucidate the selectivity and sensitivity, respectively. CN-Crown displays dual fluorescence, where the short-wavelength emission (locally excited state) mainly results from the stilbene group and the long-wavelength emission is attributed to the intramolecular charge transfer (ICT) process between electron-donor (amino) and electron-acceptor (stilbene unit). CN-Crown shows high selectivity toward Li+, while H-Crown is quenched not only by Li+ but also by Fe3+. The sensitivity of CN-Crown toward Li+ (Ksv=6.39×104M-1) is about one order higher than that of H-Crown (Ksv=6.13×103M-1). Clearly, e-withdrawing cyan group promotes ICT process in CN-Crown that leads to enhanced selectivity and sensitivity. Combination of high selectivity and sensitivity in CN-Crown promises its potential application as chemosensory materials.

Original languageEnglish
Pages (from-to)674-681
Number of pages8
JournalJournal of the Taiwan Institute of Chemical Engineers
Volume42
Issue number4
DOIs
Publication statusPublished - 2011 Jul 1

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Stilbenes
Bromine
Derivatives
Metal ions
Electrons
Charge transfer
Fluorescence
Wavelength
Crown ethers
Crown Ethers
Excited states
15-crown-5

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

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title = "Synthesis and fluorescent sensory properties of a 5-cyanostilbene derivative linked to monoaza-15-crown-5",
abstract = "To study the effect of electron-withdrawing group upon sensory characteristics of fluorescent chemosensors containing crown ether moiety (monoaza-15-crown-5), two stilbene derivatives CN-Crown and H-Crown were synthesized to compare their selectivity and sensitivity toward metal ions. CN-Crown contains two e-withdrawing groups (bromine and cyano) in stilbene unit, whereas H-Crown possesses bromine only. Fluorescence spectral variations in the presence of different metal ions or concentrations were used to elucidate the selectivity and sensitivity, respectively. CN-Crown displays dual fluorescence, where the short-wavelength emission (locally excited state) mainly results from the stilbene group and the long-wavelength emission is attributed to the intramolecular charge transfer (ICT) process between electron-donor (amino) and electron-acceptor (stilbene unit). CN-Crown shows high selectivity toward Li+, while H-Crown is quenched not only by Li+ but also by Fe3+. The sensitivity of CN-Crown toward Li+ (Ksv=6.39×104M-1) is about one order higher than that of H-Crown (Ksv=6.13×103M-1). Clearly, e-withdrawing cyan group promotes ICT process in CN-Crown that leads to enhanced selectivity and sensitivity. Combination of high selectivity and sensitivity in CN-Crown promises its potential application as chemosensory materials.",
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Synthesis and fluorescent sensory properties of a 5-cyanostilbene derivative linked to monoaza-15-crown-5. / Yu, Juin Meng; Chen, Ching Yi; Chen, Yun.

In: Journal of the Taiwan Institute of Chemical Engineers, Vol. 42, No. 4, 01.07.2011, p. 674-681.

Research output: Contribution to journalArticle

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AB - To study the effect of electron-withdrawing group upon sensory characteristics of fluorescent chemosensors containing crown ether moiety (monoaza-15-crown-5), two stilbene derivatives CN-Crown and H-Crown were synthesized to compare their selectivity and sensitivity toward metal ions. CN-Crown contains two e-withdrawing groups (bromine and cyano) in stilbene unit, whereas H-Crown possesses bromine only. Fluorescence spectral variations in the presence of different metal ions or concentrations were used to elucidate the selectivity and sensitivity, respectively. CN-Crown displays dual fluorescence, where the short-wavelength emission (locally excited state) mainly results from the stilbene group and the long-wavelength emission is attributed to the intramolecular charge transfer (ICT) process between electron-donor (amino) and electron-acceptor (stilbene unit). CN-Crown shows high selectivity toward Li+, while H-Crown is quenched not only by Li+ but also by Fe3+. The sensitivity of CN-Crown toward Li+ (Ksv=6.39×104M-1) is about one order higher than that of H-Crown (Ksv=6.13×103M-1). Clearly, e-withdrawing cyan group promotes ICT process in CN-Crown that leads to enhanced selectivity and sensitivity. Combination of high selectivity and sensitivity in CN-Crown promises its potential application as chemosensory materials.

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