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

Department of Chemistry

Seoul National University
Sungkyunkwan University
Korea University

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

14 Scopus citations

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
State	Published - 1 Sep 2016

Keywords

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

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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 = "Publisher Copyright: {\textcopyright} 2016 Published by Elsevier Ltd.",

year = "2016",

month = sep,

day = "1",

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

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

UR - https://www.scopus.com/pages/publications/84967204236

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

Keywords

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