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 journalArticlepeer-review

9 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 languageEnglish
Pages (from-to)177-183
Number of pages7
JournalDyes and Pigments
Volume135
Issue numberSI
DOIs
Publication statusPublished - Dec 2016
Event2nd International Caparica Congress on Chromogenic and Emissive Materials (IC3EM) - Caparica, Portugal
Duration: 5 Sep 20168 Sep 2016
Conference number: 2nd

Keywords

  • Detection
  • Fluorescence
  • Fluoride
  • l-serine
  • Tert-butyldimethyl silane

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