Triazolium-promoted highly selective fluorescence "turn-on" detection of fluoride ions

Jihee Cho; Illan Kim; Jong Hun Moon; Hardev Singh; Hyo Sung Jung; Jong Seung Kim; Jin Yong Lee; Sanghee Kim

doi:10.1016/j.dyepig.2016.05.005

Triazolium-promoted highly selective fluorescence "turn-on" detection of fluoride ions

Jihee Cho, Illan Kim, Jong Hun Moon, Hardev Singh, Hyo Sung Jung, Jong Seung Kim, Jin Yong Lee, Sanghee Kim

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

Through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, new pyrene-appended triazole- and triazolium-based fluorescent probes have been synthesized and their binding capabilities for anion recognition were investigated. The probes showed different fluorescence behavior in response to fluoride (F^-) ions. The probe bearing a triazolium moiety, displayed a high selectivity towards F^- ions via C-HF^- hydrogen bonding interaction and de-protonation that was accompanied by fluorescence "turn-on". Further, the experimental observations were well supported by ¹H NMR spectroscopy and density functional theory (DFT) calculations.

Original language	English
Pages (from-to)	248-254
Number of pages	7
Journal	Dyes and Pigments
Volume	132
DOIs	https://doi.org/10.1016/j.dyepig.2016.05.005
Publication status	Published - 2016 Sept 1

Bibliographical note

Funding Information:
This work was supported by the Mid-career Researcher Program (Grant No. NRF-2013R1A2A1A01015998 , S. Kim) and CRI project (Grant No. 2009-0081566 , J. S. Kim) from National Research Foundation of Korea grant funded by the Korean government (MSIP) . This work was also supported by Ministry of Science, ICT and Future Planning , subjected project to the project EDISON (Education-research Integration through Simulation On the Net, Grant No. 2012M3C1A6035359 , J. Y. Lee).

Publisher Copyright:
© 2016 Published by Elsevier Ltd.

Keywords

1,2,3-triazolium
DFT calculation
Fluorescent probe
Fluoride detection
Pyrene

ASJC Scopus subject areas

General Chemical Engineering
Process Chemistry and Technology

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10.1016/j.dyepig.2016.05.005

Cite this

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title = "Triazolium-promoted highly selective fluorescence {"}turn-on{"} detection of fluoride ions",

abstract = "Through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, new pyrene-appended triazole- and triazolium-based fluorescent probes have been synthesized and their binding capabilities for anion recognition were investigated. The probes showed different fluorescence behavior in response to fluoride (F-) ions. The probe bearing a triazolium moiety, displayed a high selectivity towards F- ions via C-HF- hydrogen bonding interaction and de-protonation that was accompanied by fluorescence {"}turn-on{"}. Further, the experimental observations were well supported by 1H NMR spectroscopy and density functional theory (DFT) calculations.",

keywords = "1,2,3-triazolium, DFT calculation, Fluorescent probe, Fluoride detection, Pyrene",

author = "Jihee Cho and Illan Kim and Moon, {Jong Hun} and Hardev Singh and Jung, {Hyo Sung} and Kim, {Jong Seung} and Lee, {Jin Yong} and Sanghee Kim",

note = "Funding Information: This work was supported by the Mid-career Researcher Program (Grant No. NRF-2013R1A2A1A01015998 , S. Kim) and CRI project (Grant No. 2009-0081566 , J. S. Kim) from National Research Foundation of Korea grant funded by the Korean government (MSIP) . This work was also supported by Ministry of Science, ICT and Future Planning , subjected project to the project EDISON (Education-research Integration through Simulation On the Net, Grant No. 2012M3C1A6035359 , J. Y. Lee). Publisher Copyright: {\textcopyright} 2016 Published by Elsevier Ltd.",

year = "2016",

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doi = "10.1016/j.dyepig.2016.05.005",

language = "English",

volume = "132",

pages = "248--254",

journal = "Dyes and Pigments",

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TY - JOUR

T1 - Triazolium-promoted highly selective fluorescence "turn-on" detection of fluoride ions

AU - Cho, Jihee

AU - Kim, Illan

AU - Moon, Jong Hun

AU - Singh, Hardev

AU - Jung, Hyo Sung

AU - Kim, Jong Seung

AU - Lee, Jin Yong

AU - Kim, Sanghee

N1 - Funding Information: This work was supported by the Mid-career Researcher Program (Grant No. NRF-2013R1A2A1A01015998 , S. Kim) and CRI project (Grant No. 2009-0081566 , J. S. Kim) from National Research Foundation of Korea grant funded by the Korean government (MSIP) . This work was also supported by Ministry of Science, ICT and Future Planning , subjected project to the project EDISON (Education-research Integration through Simulation On the Net, Grant No. 2012M3C1A6035359 , J. Y. Lee). Publisher Copyright: © 2016 Published by Elsevier Ltd.

PY - 2016/9/1

Y1 - 2016/9/1

N2 - Through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, new pyrene-appended triazole- and triazolium-based fluorescent probes have been synthesized and their binding capabilities for anion recognition were investigated. The probes showed different fluorescence behavior in response to fluoride (F-) ions. The probe bearing a triazolium moiety, displayed a high selectivity towards F- ions via C-HF- hydrogen bonding interaction and de-protonation that was accompanied by fluorescence "turn-on". Further, the experimental observations were well supported by 1H NMR spectroscopy and density functional theory (DFT) calculations.

AB - Through copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions, new pyrene-appended triazole- and triazolium-based fluorescent probes have been synthesized and their binding capabilities for anion recognition were investigated. The probes showed different fluorescence behavior in response to fluoride (F-) ions. The probe bearing a triazolium moiety, displayed a high selectivity towards F- ions via C-HF- hydrogen bonding interaction and de-protonation that was accompanied by fluorescence "turn-on". Further, the experimental observations were well supported by 1H NMR spectroscopy and density functional theory (DFT) calculations.

KW - 1,2,3-triazolium

KW - DFT calculation

KW - Fluorescent probe

KW - Fluoride detection

KW - Pyrene

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U2 - 10.1016/j.dyepig.2016.05.005

DO - 10.1016/j.dyepig.2016.05.005

M3 - Article

AN - SCOPUS:84967204236

SN - 0143-7208

VL - 132

SP - 248

EP - 254

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

Triazolium-promoted highly selective fluorescence "turn-on" detection of fluoride ions

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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