The confidence of blue: A new highly selective bio-inspired coumarin emissive probe for fluoride recognition

Augusto C. Gonçalves; Nayara C. Sato; Hugo M. Santos; José Luis Capelo; Carlos Lodeiro; Alcindo A. dos Santos

doi:10.1016/j.dyepig.2016.02.032

The confidence of blue: A new highly selective bio-inspired coumarin emissive probe for fluoride recognition

Augusto C. Gonçalves, Nayara C. Sato, Hugo M. Santos, José Luis Capelo, Carlos Lodeiro, Alcindo A. dos Santos

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

12 Citations (Scopus)

Abstract

A new fluorogenic probe for fluoride anion detection was designed and synthetized accomplishing by the linkage between a Coumarin-440 and a Boc-Ser(TBDMS)-OH via amide bond formation. The photophysical properties and the selectivity for fluoride detection, among a range of anions (Cl^-, Br^-, I^-, BF₄ ^-, NO₃ ^-, ClO₄ ^-, PF₆ ^-, HSO₄ ^-, CN^-, OAc^-), was explored. The sensing mechanism was proposed and supported by ¹H NMR and MALDI-MS experiments. A reaction triggered by the nucleophilic attack of the fluoride anion to the silicon atom of the tert-buthyldimethylsilane (TBDMS) group was responsible for the disruption of OSi bond, which generates an emissive species. UV-vis absorption, fluorescence steady state, and time resolved emission spectroscopy were employed. The lowest quantity of detectable amount of 3.3 μmol/L for F^- was achieved for fluorescence measurements in acetonitrile solution. The system could be adapted to paper discs under a UV lamp (365 nm) for direct visual fluoride ion detection.

Original language	English
Pages (from-to)	177-183
Number of pages	7
Journal	Dyes and Pigments
Volume	135
Issue number	SI
DOIs	https://doi.org/10.1016/j.dyepig.2016.02.032
Publication status	Published - Dec 2016
Event	2nd International Caparica Congress on Chromogenic and Emissive Materials (IC3EM) - Caparica, Portugal Duration: 5 Sept 2016 → 8 Sept 2016 Conference number: 2nd

Keywords

Detection
Fluorescence
Fluoride
l-serine
Tert-butyldimethyl silane

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10.1016/j.dyepig.2016.02.032Licence: CC BY-NC-ND

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title = "The confidence of blue: A new highly selective bio-inspired coumarin emissive probe for fluoride recognition",

abstract = "A new fluorogenic probe for fluoride anion detection was designed and synthetized accomplishing by the linkage between a Coumarin-440 and a Boc-Ser(TBDMS)-OH via amide bond formation. The photophysical properties and the selectivity for fluoride detection, among a range of anions (Cl-, Br-, I-, BF4 -, NO3 -, ClO4 -, PF6 -, HSO4 -, CN-, OAc-), was explored. The sensing mechanism was proposed and supported by 1H NMR and MALDI-MS experiments. A reaction triggered by the nucleophilic attack of the fluoride anion to the silicon atom of the tert-buthyldimethylsilane (TBDMS) group was responsible for the disruption of OSi bond, which generates an emissive species. UV-vis absorption, fluorescence steady state, and time resolved emission spectroscopy were employed. The lowest quantity of detectable amount of 3.3 μmol/L for F- was achieved for fluorescence measurements in acetonitrile solution. The system could be adapted to paper discs under a UV lamp (365 nm) for direct visual fluoride ion detection.",

keywords = "Detection, Fluorescence, Fluoride, l-serine, Tert-butyldimethyl silane",

author = "Gon{\c c}alves, {Augusto C.} and Sato, {Nayara C.} and Santos, {Hugo M.} and Capelo, {Jos{\'e} Luis} and Carlos Lodeiro and {dos Santos}, {Alcindo A.}",

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AU - Gonçalves, Augusto C.

AU - Sato, Nayara C.

AU - Santos, Hugo M.

AU - Capelo, José Luis

AU - Lodeiro, Carlos

AU - dos Santos, Alcindo A.

N1 - Conference code: 2nd

PY - 2016/12

Y1 - 2016/12

N2 - A new fluorogenic probe for fluoride anion detection was designed and synthetized accomplishing by the linkage between a Coumarin-440 and a Boc-Ser(TBDMS)-OH via amide bond formation. The photophysical properties and the selectivity for fluoride detection, among a range of anions (Cl-, Br-, I-, BF4 -, NO3 -, ClO4 -, PF6 -, HSO4 -, CN-, OAc-), was explored. The sensing mechanism was proposed and supported by 1H NMR and MALDI-MS experiments. A reaction triggered by the nucleophilic attack of the fluoride anion to the silicon atom of the tert-buthyldimethylsilane (TBDMS) group was responsible for the disruption of OSi bond, which generates an emissive species. UV-vis absorption, fluorescence steady state, and time resolved emission spectroscopy were employed. The lowest quantity of detectable amount of 3.3 μmol/L for F- was achieved for fluorescence measurements in acetonitrile solution. The system could be adapted to paper discs under a UV lamp (365 nm) for direct visual fluoride ion detection.

AB - A new fluorogenic probe for fluoride anion detection was designed and synthetized accomplishing by the linkage between a Coumarin-440 and a Boc-Ser(TBDMS)-OH via amide bond formation. The photophysical properties and the selectivity for fluoride detection, among a range of anions (Cl-, Br-, I-, BF4 -, NO3 -, ClO4 -, PF6 -, HSO4 -, CN-, OAc-), was explored. The sensing mechanism was proposed and supported by 1H NMR and MALDI-MS experiments. A reaction triggered by the nucleophilic attack of the fluoride anion to the silicon atom of the tert-buthyldimethylsilane (TBDMS) group was responsible for the disruption of OSi bond, which generates an emissive species. UV-vis absorption, fluorescence steady state, and time resolved emission spectroscopy were employed. The lowest quantity of detectable amount of 3.3 μmol/L for F- was achieved for fluorescence measurements in acetonitrile solution. The system could be adapted to paper discs under a UV lamp (365 nm) for direct visual fluoride ion detection.

KW - Detection

KW - Fluorescence

KW - Fluoride

KW - l-serine

KW - Tert-butyldimethyl silane

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M3 - Article

AN - SCOPUS:84962046058

SN - 0143-7208

VL - 135

SP - 177

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JO - Dyes and Pigments

JF - Dyes and Pigments

IS - SI

Y2 - 5 September 2016 through 8 September 2016

ER -

The confidence of blue: A new highly selective bio-inspired coumarin emissive probe for fluoride recognition

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Keywords

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